Acetic Acid → (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

HRID 1087662Notes

Reaction equation

HRID 1087662 reaction equation
C[Li].[CH:3]1([C@:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([OH:13])[C:10]([OH:12])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:20](O)(=O)C.O>CCOCC.C1COCC1>[CH:3]1([C@@:9]([OH:13])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 777377Cyclohexylphenylglycolic acid, (-)-HCID 178418348HCID 178418348, compound

Product 1

HCID 15030055(R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 315 ml of 1.4M CH3Li (0.44 mole) in ether and 750 ml of THF at room temperature was added a solution of 26 g (0.11 mole) of (R)-cyclohexylmandelic acid, prepared by the method of R. B. Barlow, F. M. Franks, and J. D. M. Pearson, J. Med. Chem., 16, 439 (1973), in THF. Following the addition, the mixture was stirred at room temperature for 3.5 hours and then brought to reflux for 3 hours. The mixture was cooled and then added dropwise to a mixture of 300 ml of glacial acetic acid and 700 ml of water. This mixture was extracted with ether, the organic layer was separated, washed with water and saturated aqueous sodium bicarbonate, dried, and the solvent removed. The mixture was distilled to give 20 g of clear oil (bp 120° C., 0.1 mm Hg), NMR (chloroform-d) δ7.5(m, 5H), 4.5(S, 1H), 2.4(t, 1H), 2.0(s, 3H), 1.9-1.0(m, 10H).

Workup

  1. customprepared by the method of R
  2. additionthe addition
  3. temperatureto reflux for 3 hours
  4. temperatureThe mixture was cooled
  5. extractionThis mixture was extracted with ether
  6. customthe organic layer was separated
  7. washwashed with water and saturated aqueous sodium bicarbonate
  8. customdried
  9. customthe solvent removed
  10. distillationThe mixture was distilled

Sources & evidence

ORD record
ord-d1c5336e13e64664b508272c15d968ac
Source dataset
uspto-grants-1991_07
Patent number
US05036107

Reaction notes

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