Toluene → Methyl cyclopentylmandelate

HRID 377785Notes

Reaction equation

HRID 377785 reaction equation
[C:1]1([C:7](=[O:12])[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=CC=1>>[C:1]1([C:7]([CH:16]2[CH2:17][CH2:18][CH2:13][CH2:19]2)([OH:12])[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 84835Methyl phenylglyoxalate

Product 1

HCID 89233Methyl cyclopentylmandelateYield 76.9%

Procedure

Using the same method as described for (1) of example 3, raw materials at equal weight were added successively. The difference was using a reaction temperature of -10-6° C. during dropuise addition of the toluene solution of 82 g of methyl phenylglyoxylate to cyclopentadiene Grignard reagent. 90 g of methyl 2-phenyl-2-cyclopentyl-2-hydroxy-acetate was obtained in 76.9% yield, nD25 1.5203, boiling point 82-5° C./0.03 mmHg. Silicagel GF 254 thin layer plate; developer: 1,2-dichloroethane, ultraviolet 254 nm fluorescence localization, main spot: Rf=0.72, without impurity spot.

Workup

  1. additionwere added successively
  2. customa reaction temperature of -10-6° C.

Sources & evidence

ORD record
ord-d8ef3ad9084b403cafa4c3128e04c734
Source dataset
uspto-grants-2000_02
Patent number
US06028198

Reaction notes

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