Acetic Acid → 3-(2-Oxo-1-phenylcyclohexyl)propanoic acid

HRID 71227Notes

Reaction equation

HRID 71227 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1([CH2:14]CC#N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[C:19]([OH:22])(=[O:21])[CH3:20]>Cl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1([CH2:14][CH2:20][C:19]([OH:22])=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962Water2×HCID 2633833-(2-Oxo-1-phenylcyclohexyl)propanenitrile

Product 1

HCID 2008413-(2-Oxo-1-phenylcyclohexyl)propanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-(2-oxo-1-phenylcyclohexyl)propanenitrile (5.05 g, 22.22 mmol) in acetic acid (11.1 mL), conc. HCl (33.2 mL), and water (11.1 mL) was refluxed for 16 h under N2, cooled to room temperature, and poured into water (66 mL). The product separated out as an layer of oil. The suspension was cooled to 0° C. in an ice bath for 30 min. with occasional swirling and the crystallized product was collected by filtration and rinsed several times with water, and dried in vacuo to obtain 3-(2-oxo-1-phenylcyclohexyl)propanoic acid (1B, 4.77 g, 85% yield) as a white crystalline solid. HPLC: tR=2.47 min, YMC Combiscreen ODS-A 4.6×50 mm, 4 min gradient, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH—0.1% TFA; Final solvent: 90% aq. MeOH—0.1% TFA. LC/MS: m/e 247.2 (M+H)+, 229.2 (M+H−H2O)+.

Workup

  1. temperaturewas refluxed for 16 h under N2
  2. customThe product separated out as an layer of oil
  3. temperatureThe suspension was cooled to 0° C. in an ice bath for 30 min.
  4. filtrationthe crystallized product was collected by filtration
  5. washrinsed several times with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-27ab3af6b7c34eab8931c037cf0cf997
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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