Water → ((cyclohex-2-enyloxy)methyl)benzene

HRID 74985

Reaction equation

[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[H-].[Na+].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C1COCC1.CCOCC>[CH:1]1([O:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of cyclohex-2-en-1-ol (10.0 g, 101.9 mmol) in anhydrous THF (100 mL) was added to a stirred suspension containing sodium hydride (8.0 g, 199.7 mmol) (60% dispersion in oil) and benzyl bromide in anhydrous THF (250 mL) maintained at 50° C. The resulting solution was stirred at 55-60° C. for 18 h. After cooling to ambient temperature, water was added to quench the reaction and the mixture was diluted with ether (500 mL). The organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo to an oil that was subjected to a short silica plug filtration to provide 16.1 g of desired product 51a that was used directly in the next step without further purification.

Workup

temperatureAfter cooling to ambient temperature
customto quench
customthe reaction
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo to an oil that
filtrationwas subjected to a short silica plug filtration

Sources & evidence

ORD record: ord-4551983249644db0ac1b7f9159ed7a96
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829007B2

Linked notes

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