Water → Methyl cyclopentylmandelate

HRID 495048Notes

Reaction equation

HRID 495048 reaction equation
[CH:1]1([C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:10])[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C.C(Cl)Cl.CCCCCC>[CH:1]1([C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:10])[C:7]([O:9][CH3:17])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 98283alpha-Cyclopentylmandelic acid

Product 1

HCID 89233Methyl cyclopentylmandelate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a mixture of (−)-cyclopentylmandelic acid, R(−)1, (1.83 g, 8.3 mmol) and potassium carbonate (2.87 g, 21 mmol) in DMF (21 ml), methyl iodide (3.53 g, 25 mmol) was added at room temperature. The mixture was stirred at room temperature for 2 h, and then poured into water and extracted with hexane three times. Evaporation of dried hexane extract gave a crude product. Flash chromatography of the crude product on silica gel with 1.5:1 hexane:methylene chloride gave pure product R(−)2 (1.90 g, 95%). 1H NMR (CDCl3, 300 MHz): 1.32-1.36, 1.43-1.61 [8H, m, (CH2)4], 2.90 [1H, p, CHC(OH)], 3.71 (1H, s, OH), 3.79 (3H, s, CH3), 7.25-7.28, 7.31-7.35, 7.63-7.65 (5H, m, Ph) ppm.

Workup

  1. extractionextracted with hexane three times
  2. customEvaporation of dried hexane
  3. extractionextract
  4. customgave a crude product

Sources & evidence

ORD record
ord-545ff585baf64d018f50c5011a70c64f
Source dataset
uspto-grants-2009_05
Patent number
US07538219B2

Reaction notes

Loading…