Methyl iodide → Methyl cyclohexylphenylglycolate, (-)-

HRID 1489217Notes

Reaction equation

HRID 1489217 reaction equation
[CH:1]1([C@@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O.O>[CH:11]1([C@@:7]([OH:17])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:10][CH3:18])=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 777377Cyclohexylphenylglycolic acid, (-)-

Product 1

HCID 10999395Methyl cyclohexylphenylglycolate, (-)-Yield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of (R)-α-cyclohexyl-α-hydroxybenzeneacetic acid (III) (12.2 g, 52.1 mmol) and K2CO3 (10.8 g, 78.2 mmol) in 100 mL of acetone was added methyl iodide (MeI) (13.0 mL, 208 mmol) dropwise at 0° C. (ice bath). After the addition (ca. 1 h) of MeI, the reaction mixture was stirred at room temperature overnight. The mixture was filtered through a pad of Celite and rinsed with acetone twice. The filtrate was concentrated to give a white slurry which was diluted with water and extracted with heptane. The combined extracts were washed with water, brine, dried and concentrated to give the product (R)-IV (11.9 g, 92% yield) as a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washrinsed with acetone twice
  3. concentrationThe filtrate was concentrated
  4. customto give a white slurry which
  5. extractionextracted with heptane
  6. washThe combined extracts were washed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. customto give the product (R)-IV (11.9 g, 92% yield) as a white solid

Sources & evidence

ORD record
ord-315d0f2d6af9406f96f522adf4f3b5ca
Source dataset
uspto-grants-1997_10
Patent number
US05677346

Reaction notes

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