1. Single Step

92%

Overview

Steps/Stages Notes

1.1R:H2O, C:879132-91-9, S:Me2CHOH, 6 h, 80-95°C

chemoselective, Reactants: 1, Reagents: 1, Catalyst: 1, Solvent: 1, Steps: 1, Stages: 1, Most stages in any one step: 1

References

Kinetic, Spectroscopic, and X-Ray Crystallographic Evidence for the Cooperative Mechanism of the Hydration of Nitriles Catalyzed by a Tetranuclear Ruthenium-μ-oxo-μ-hydroxo Complex

By Yi, Chae S. et al

From Organometallics, 27(9), 2030-2035; 2008

Experimental Procedure

General/Typical Procedure: General Procedure of the Catalytic Nitrile Hydration Reaction. A nitrile substrate (2.0 mmol), H2O (10-20 equiv), and 2-3 mL of solvent were placed in a 25 mL Schlenk tube equipped with a magnetic stirring bar and Teflon stopcock. After the reaction tube was degassed in a dry ice/acetone bath, the reaction tube was brought into the glovebox. The catalyst 1 (34 mg, 1 mol %) was added to the reaction tube. The tube was brought out of the glovebox and was stirred in an oil bath at 80-95 °C for 6-20 h. After the reaction was completed, the reaction tube was opened to air and the solution was filtered through a small pad of Celite. Analytically pure product was isolated by simple recrystallization (i-PrOH/ hexanes or EtOH/benzene) or by column chromatography on silica gel (EtOAc/hexanes). 2e: 2e: 1H NMR (CDCl3/DMSO-d6, 300 MHz) δ 7.37 (m, 2 H, Arortho), 7.29 (m, 3 H, Arpara and meta), 5.56 (br d, NH2), 3.59 (s, CH2); 13C{1H} NMR (CDCl3/DMSO-d6, 100 MHz) δ 173.8 (C=O), 135.4, 129.5, 129.0, and 127.3 (Ar carbons), 43.3 (CH2); GC-MS m/z = 152 (M+).

2. Single Step

88%

Overview

Steps/Stages Notes

1.1R:NH3, S:H2O

Reactants: 1, Reagents: 1, Solvent: 1, Steps: 1, Stages: 1, Most stages in any one step: 1

References

A process for the manufacture of p-hydroxyphenylacetamide from p-hydroxyacetophenone

By Kumar, Ashok et al

From Indian, 171707, 19 Dec 1992

6. Single Step

67%

Overview

Steps/Stages Notes

1.1R:EtOH, R:H2SO4

1.2R:NH3, S:H2O

Reactants: 1, Reagents: 3, Solvent: 1, Steps: 1, Stages: 2, Most stages in any one step: 2

References

Synthesis of atenolol from benzylcyanide

By Wei, Chang-mei

From Huaihai Gongxueyuan Xuebao, 9(2), 36-38; 2000

7. Single Step

65%

Overview

Steps/Stages Notes

1.1R:S, R:NH3, S:Me2CHOH

thermal, 160°, hastelloy C autoclave, Reactants: 1, Reagents: 2, Solvent: 1, Steps: 1, Stages: 1, Most stages in any one step: 1

References

Preparation of aromatic acetamides from aryl methyl ketones

By Mott, Graham N.

From U.S., 5041657, 20 Aug 1991

8. Single Step

Overview

Steps/Stages Notes

1.1R:SOCl2, S:DMF, rt → reflux

1.2R:NH4OH, rt

chemoselective, Reactants: 1, Reagents: 2, Solvent: 1, Steps: 1, Stages: 2, Most stages in any one step: 2

References

Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives

By Moon, Jong Taik et al

From Bioorganic & Medicinal Chemistry Letters, 20(2), 734-737; 2010

9. Single Step

Overview

Steps/Stages Notes

1.1R:

i-PrN=C=NPr-i, R:1-Benzotriazolol, S:CH2Cl2, S:DMF, 1 h, rt

1.2R:F3CCO2H, S:CH2Cl2

solid-supported reaction, first stage is attachment to Rink resin, Reactants: 1, Reagents: 3, Solvent: 2, Steps: 1, Stages: 2, Most stages in any one step: 2

References

Efficient Remote Axial-to-Central Chirality Transfer in Enantioselective SmI2-Mediated Reductive Coupling of Aldehydes with Crotonates of Atropisomeric 1-Naphthamides

By Zhang, Yan et al

From Journal of Organic Chemistry, 71(6), 2445-2455; 2006

Experimental Procedure

General/Typical Procedure: Preparation of the Resin-Bound Phenol, 34b. Rink amide resin (0.7 mmol/g) was treated with a solution of 20% piperidine in DMF for 1 h at room temperature and then washed with DMF and CH2- Cl2. The washing procedure was repeated five times, and the resin was dried overnight in vacuo. 4-Hydroxyphenylacetic acid (33b; 5.0 equiv) was coupled to the above pretreated resin by using DIC(5.0 equiv) and HOBt (5.5 equiv) in DMF-CH2Cl2 (1:1) at room temperature for 1 h, followed by washing with DMF and CH2Cl2 (repeated five times). The resin-bound phenol was dried overnight in vacuo. A resin-free sample of the attached phenol (as 4-hydroxyphenyl acetamide) was obtained after cleavage from the resin by treating with 20% CF3CO2H in CH2Cl2. The loading of the resinbound phenol 34b is estimated to be 0.45 mmol/g by the increased weight. 4-Hydroxyphenyl acetamide phenol 34b

11. Single Step

67%

Overview

Steps/Stages Notes

1.1 R: R:S, R:NH4OH, S:Me2CHOH

Classification: Migration; Oxidation; C-Amination; # Conditions: S+S(NH4)n i-PrOH; 160 deg 12h; # Comments: Willgerodt reaction; other examples, Reactants: 1, Reagents: 3, Solvent: 1, Steps: 1, Stages: 1, Most stages in any one step: 1

References

Preparation of hydroxyphenylalkanoic acids by the Willgerodt reaction

By Ott, Arnold C. et al

From Journal of the American Chemical Society, 68, 2633-4; 1946

Hi,

Unfortunately I can't get it for you.. Usually, using SciFinder Web, I can type in the title of the patent (i.e. "A process for the manufacture of p-hydroxyphenylacetamide from p-hydroxyacetophenone") in to the Explore References window, and get a long list of responses; only the first response will have the whole title intact, plus it wll have a "Full Text" button. All this happened, but the response this time did not contain the "Dowload original" button. If you can find a company which uses SciFinder, their search may be down-loadable.

Sorry,

Bill