Sodium Hydroxide → (4,4-Dimethyl-cyclohexyl)-acetic acid

HRID 1045069Notes

Reaction equation

C[O:2][C:3](=[O:13])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][CH2:6]1.[OH-].[Na+]>>[CH3:11][C:8]1([CH3:12])[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:13])=[O:2])[CH2:10][CH2:9]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 67179717HCID 67179717, compound

Product 1

HCID 64417213(4,4-Dimethyl-cyclohexyl)-acetic acidYield 95%

Procedure

Hydrolysis of (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg, 0.43 mmol) with NaOH following a method analogous to General Procedure G1 gave (4,4-dimethyl-cyclohexyl)-acetic acid after purification (70 mg, 95% yield). This acid (70 mg) was converted to 1-(4,4-dimethyl-cyclohexyl)-propan-2-one (60.0 mg, 89% yield) using MeLi in ethyl ether following a method analogous to General Procedure A1. Pyrrolidone hydrotribromide (190 mg, 0.38 mmol) treatment of the above ketone following a method analogous to General Procedure B1 gave 1-bromo-3-(4,4-dimethyl-cyclohexyl)-propan-2-one (70 mg).

Sources & evidence

ORD record: ord-c0d8af4af13b4fe39f5da9ba55635a57
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563742B2

Reaction notes

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