Water → 2-(3,4-Dimethoxy-alpha-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal

HRID 974109Notes

Reaction equation

C([Li])CCC.[CH3:6][O:7][CH:8]([O:21][CH3:22])[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH:28]=[O:29].O>CCCCCC.O1CCCC1.C(OCC)(=O)C>[CH3:22][O:21][CH:8]([O:7][CH3:6])[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[C:10]=1[CH:28]([OH:29])[C:27]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:25]([O:24][CH3:23])[CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

136 ml of a 1.6M n-butyl lithium solution in hexane are added to a solution of 48.5 g of 3,4,5-trimethoxybenzaldehyde dimethyl acetal in 485 ml of tetrahydrofuran under stirring at 0° C. for about 20 minutes. The mixture is further stirred at 0° C. for 30 minutes, and 33.2 g of 3,4-dimethoxybenzaldehyde are added thereto. After stirring the mixture at 0° to 10° C. for 2 hours, 780 ml of water and 780 ml of ethyl acetate are added thereto. After shaking the mixture, the organic layer is separated therefrom, washed with water and evaporated under reduced pressure to remove solvent. 81.0 g of 2-(3,4-dimethoxy-α-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal are thereby obtained as a yellow oil.

Workup

stirringThe mixture is further stirred at 0° C. for 30 minutes
stirringAfter stirring the mixture at 0° to 10° C. for 2 hours
stirringAfter shaking the mixture
customthe organic layer is separated
washwashed with water
customevaporated under reduced pressure
customto remove solvent

Sources & evidence

ORD record: ord-47a8221465804eb9aff05e71986d1b1c
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05066825

Reaction notes

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