Water → Methyl cyclopentylmandelate

HRID 469142Notes

Reaction equation

HRID 469142 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>[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

7

Reactant 4

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

Product 1

HCID 89233Methyl cyclopentylmandelateYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of racemic cyclopentylmandelic acid R/S(±)1 (4.47 g, 20 mmol) and potassium carbonate (7.01 g, 50 mmol) in DMF (50 ml), methyl iodide (8.64 g, 60 mmol) was added at room temperature. The mixture was stirred at room temperature for 2 h, and then poured into water and extracted with hexanes three times. Evaporation of the dried hexanes extract gave a crude product. Flash chromatography of the crude product on silica gel with 1.5:1 hexanes:methylene chloride gave the pure product 2 (3.02 g, 64%). 1H NMR (CDCl3, 300 MHz): 1.32-1.37, 1.43-1.69 [8H, m, (CH2)4], 2.90 [1H, p, CHC(OH)], 3.74 (1H, s, OH), 3.77 (3H, s, CH3), 7.25-7.37, 7.63-7.65 (5H, m, Ph) ppm.

Workup

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

Sources & evidence

ORD record
ord-45f29870e98748ed81fb3355b8becaa2
Source dataset
uspto-grants-2014_01
Patent number
US08628759B2

Reaction notes

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