Sodium Hydroxide → 2-(4-tert-Butylcyclohexyl)acetic acid

HRID 2268751

Reaction equation

HRID 2268751 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6]1.[OH-].[Na+]>CO>[C:11]([CH:8]1[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:15])=[O:2])[CH2:6][CH2:7]1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12808867Methyl 2-(4-tert-butylcyclohexyl)acetate

Product 1

HCID 41507362-(4-tert-Butylcyclohexyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-tert-Butylcyclohexyl)acetic acid methyl ester (9.81 g, 46.5 mmol) was dissolved in methanol 950 ml) and cooled on an ice bath. 2M Sodium hydroxide solution (50 ml, 100 mmol) was added with stirring. When addition was complete the reaction mixture was allowed to warm to room temperature and was stirred overnight. The methanol was evaporated in vacuo and the remaining aqueous phase was acidified to pH1 with 1M hydrochloric acid. The aqueous phase was then extracted with ethyl acetate(3×). The organic extracts were combined, dried over magnesium sulphate, filtered and evaporated to give a white solid, (8.66 g, 94%). 1H-NMR δ (CDCl3) (as a mixture of cis-trans isomers), 2.43 (0.1 H, d, J=8 Hz), 2.24 (0.9H, d, J=7 Hz), 1.92-1.47 (5H, m), 1.18-0.90 (5H, m) and 0.87 (9H, s).

Workup

  1. temperaturecooled on an ice bath
  2. additionWhen addition
  3. stirringwas stirred overnight
  4. customThe methanol was evaporated in vacuo
  5. extractionThe aqueous phase was then extracted with ethyl acetate(3×)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a white solid, (8.66 g, 94%)

Sources & evidence

ORD record
ord-517e140fdb20439f84956e1d88366a6b
Source dataset
uspto-grants-2001_12
Patent number
US06329373B1

Linked notes

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