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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561482Generated: October 31, 2026

Water → 2-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

https://huagongshe.com/reaction/561482

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium borohydrideHCID 4311764—
Reactant2-(4-Methylbenzoyl)cyclopropanecarbonitrileHCID 58392415—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product2-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrileHCID 58392344—

Reaction Conditions

Temperature40 °C

Reaction Steps

607 mg (16.0 mmol) of sodium borohydride were added to 2.70 g (14.6 mmol) of the compound from Example 126A in 60 ml of ethanol and 16 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to water and extracted with dichloromethane, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 2.56 g (94% of theory) of a mixture of the diastereomers of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08063234B2
Source datasetuspto-grants-2011_11
ORD IDord-813536802ef449fca12bbcf7d7b84346
Source noteuspto-grants-2011_11