Potassium hydroxide methanol → HCID 178445617, compound

HRID 653974Notes

Reaction equation

HRID 653974 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:9][CH2:8]1)C.[OH-].[K+].CO>CO.O>[CH3:16][C:13]([C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][CH2:5][C:4]([OH:17])=[O:3])[CH2:12][CH2:11]1)([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 23689386Potassium hydroxide methanolHCID 178471541HCID 178471541, compound

Product 1

HCID 178445617HCID 178445617, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirring solution of trans-4-(1,1-dimethylethyl)cyclohexanepropanoic acid ethyl ester (3.58 g, 14.9 mmol) in CH3OH (198 mL) at 0° C. were added 10% KOH/MeOH (46 mL), followed by H2O (30 mL). The mixture was stirred at room temperature 5 h, then diluted with H2O (20 mL) and concentrated. The residue was diluted with H2O (20 mL) and ice chips and the mixture was acidified to pH 2 with 3N HCl. The aqueous solution was extracted with ethyl ether (4×150 mL). The combined organic extracts were washed with brine (200 mL), dried (Na2SO4) and concentrated to give crystalline trans-4-(1,1-dimethylethyl)cyclohexanepropanoic acid (3.09 g, 14.5 mmol) in 98% yield mp 105°-107° C.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with H2O (20 mL) and ice chips
  3. extractionThe aqueous solution was extracted with ethyl ether (4×150 mL)
  4. washThe combined organic extracts were washed with brine (200 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0f97f5bb7b1c469a9b6437155243b3c0
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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