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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1596813Generated: October 29, 2026

Diethyl Ether → 1-Allyl-1-cyclohexanol

https://huagongshe.com/reaction/1596813

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantCyclohexanoneHCID 7967—
Reactant3-tert-butyl-2,2-dimethylhex-5-en-3-olHCID 11789902—
ReactantButyllithiumHCID 178418339—
CatalystZinc bromideHCID 10421208—
SolventPentaneHCID 8003—
SolventTetrahydrofuranHCID 8028—
Product1-Allyl-1-cyclohexanolHCID 79145—

Reaction Steps

1.94 ml of a 1.4-molar solution of n-butyllithium (2.71 mmol) in pentane were added dropwise at 0° C. under argon for 2 minutes to a stirred solution of 500 mg (2.71 mmol) 3-tert-butyl-2,2-dimethylhex-5-en-3-ol in 4 ml THF. The solution obtained was stirred for 15 minutes, and then a solution of 610 mg (2.71 mmol) ZnBr2 in 2 ml THF and 280 μl (2.71 mmol) cyclohexanone were added. The reaction mixture was stirred for 4 hours and heated to room temperature. Subsequently, it was processed analogous to Example 1. The raw product obtained was cleaned by means of a silica column with 20% diethyl ether/light gasoline. There was obtained the alcohol as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06291713B1
Source datasetuspto-grants-2001_09
ORD IDord-caa7db11a90040bcae87846bb6b1a124
Source noteuspto-grants-2001_09