Dimethylformamide → 4-(Benzyloxy)-2-ethylbenzaldehyde

HRID 1394697Notes

Reaction equation

[Li]CCCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][C:14]=1[CH2:27][CH3:28].CN(C)[CH:31]=[O:32].[NH4+].[Cl-]>C1COCC1>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:31]=[O:32])=[C:14]([CH2:27][CH3:28])[CH:15]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -85 °C

Procedure

A 1.6 M solution of n-BuLi in hexane (44.4 ml, 69.9 mmol) was added within 10 min to a stirred cooled (−85° C.) solution of 1-bromo-2-ethyl-4-(phenylmethoxy)-benzene (18.5 g, 63.5 mmol) in dry THF (22 ml). The mixture was stirred for 1 h at −85° C. under an argon atmosphere. N,N-Dimethylformamide (25.5 ml, 330.4 mmol) was added and the temperature was allowed to rise slowly to room temperature. An aqueous saturated NH4Cl solution (70 ml) was added under ice cooling. The mixture was extracted two times with dichloromethane, the combined extracts were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to yield 11.9 g (49.5 mmol, 78%) of the title compound as yellow oil.

Workup

customto rise slowly to room temperature
extractionThe mixture was extracted two times with dichloromethane
washthe combined extracts were washed with brine
dry with materialdried over sodium sulfate
customRemoval of the solvent under reduced pressure
customgave a yellow oil which
customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)

Sources & evidence

ORD record: ord-5b33057683fa4ec180b0b44fd1f75fac
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348349B2

Reaction notes

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