Lithium hydroxide, monohydrate → 1-Benzylcyclopentane-1-carboxylic acid

HRID 393413Notes

Reaction equation

HRID 393413 reaction equation
C([O:3][C:4]([C:6]1([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>C1COCC1.CO.O>[CH2:11]([C:6]1([C:4]([OH:5])=[O:3])[CH2:10][CH2:9][CH2:8][CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 153113771-Benzylcyclopentane carboxylic acid ethyl ester

Product 1

HCID 226601311-Benzylcyclopentane-1-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-benzylcyclopentane carboxylic acid ethyl ester (0.40 g, 1.7 mmol) in 10 mL of THF and 5 mL of methanol was treated with a solution of 200 mg of lithium hydroxide hydrate in 5 mL of water and the mixture was stirred for 3 days at room temperature and at 40° C. for 3 days. The mixture was diluted with water, washed with ether and acidified with excess 6 N HCl. The aqueous layer was extracted with ether and the combined extracts were washed with water and brine and were dried (MgSO4). Evaporation gave 0.34 g (96%) of 1-benzylcyclopentane carboxylic acid as a thick yellow oil.

Workup

  1. washwashed with ether
  2. extractionThe aqueous layer was extracted with ether
  3. washthe combined extracts were washed with water and brine
  4. dry with materialwere dried (MgSO4)
  5. customEvaporation

Sources & evidence

ORD record
ord-8a1271d20a294391a502bdd0aeabed6d
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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