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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561476Generated: October 31, 2026

Diethyl Ether → 2-Chloro-alpha-cyclopropyl-4-methylbenZenemethanol

https://huagongshe.com/reaction/561476

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantAmmonium ChlorideHCID 25517—
ReactantSodium borohydrideHCID 4311764—
Reactant(2-Chloro-4-methylphenyl)(cyclopropyl)methanoneHCID 13175620—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product2-Chloro-alpha-cyclopropyl-4-methylbenZenemethanolHCID 58392529126.9%

Reaction Conditions

Temperature40 °C

Reaction Steps

51.3 mg (1.36 mmol) of sodium borohydride were added to 320 mg (1.23 mmol) of the compound from Example 125A in 5 ml of ethanol and 1 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. Then a further 46.6 mg (1.23 mmol) of sodium borohydride were added, and the mixture was stirred at 40° C. overnight. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 307 mg of the title compound were obtained and were reacted without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08063234B2
Source datasetuspto-grants-2011_11
ORD IDord-f0acd68b546c4d2e8aa9d674f233bcf2
Source noteuspto-grants-2011_11