Potassium Hydroxide → 3-(1-Phenylcyclohexyl)propanoic acid

HRID 714240Notes

Reaction equation

O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[K+].O.NN>C(O)CO>[C:8]1([C:3]2([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:2]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 3-(2-oxo-1-phenylcyclohexyl)propanoic acid (1 g, 4.06 mmol), potassium hydroxide (0.770 g, 13.72 mmol), hydrazine monohydrate (0.348 mL, 6.09 mmol), and ethylene glycol (5 mL) was heated to 130° C. for 1.5 h. The condenser was removed and the mixture was heated to 200° C. for 30 min. The reaction mixture was then heated under reflux with a reflux condenser for additional 1.5 h. The reaction mixture was cooled to room temperature and diluted with 1N HCl to a total reaction volume of 25 mL. The precipitated product was collected by filtration, washed several times with water, and dried in vacuo to obtain 3-(1-phenylcyclohexyl) propanoic acid as a white solid (Int. 2, 923 mg, 93% yield). HPLC: tR=3.7 min, Chromolith SpeedRod 4.6×50 mm, 4 min gradient, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH-0.2% H3PO4; Final solvent: 90% aq. MeOH-0.2% H3PO4. LC/MS: m/e 215.19 (M+H-H2O)+.

Workup

customThe condenser was removed
temperaturethe mixture was heated to 200° C. for 30 min
temperatureThe reaction mixture was then heated
temperatureunder reflux with a reflux condenser for additional 1.5 h
temperatureThe reaction mixture was cooled to room temperature
additiondiluted with 1N HCl to a total reaction volume of 25 mL
filtrationThe precipitated product was collected by filtration
washwashed several times with water
customdried in vacuo

Sources & evidence

ORD record: ord-1776712fab244dc0955ec88584648612
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187437B2

Reaction notes

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