Water → 5-Bromo-6,6'-dimethyl-2,2', 3', 4'-tetramethoxybenz-hydryl alcohol

HRID 1884916Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1Br.BrCCBr.[Br:19][C:20]1[CH:21]=[CH:22][C:23]([O:29][CH3:30])=[C:24]([C:27]=1[CH3:28])[CH:25]=[O:26].O>O1CCCC1>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([O:29][CH3:30])=[C:24]([C:27]=1[CH3:28])[CH:25]([OH:26])[C:4]1[C:5]([CH3:13])=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1]

Participants

Conditions

Temperature: 30 °C

Procedure

2.36 g of 2,3,4-trimethoxy-6-methylbromobenzene and 0.32 g of agnesium turnings were initially charged in 5 ml of anhydrous tetrahydrofuran, 0.57 ml of 1,2-dibromoethane was added and the reaction mixture was heated at reflux temperature for about 40 min. After cooling to 30° C., 1.40 g of 5-bromo-2-methoxy-6-methylbenzaldehyde were added dropwise, and the solution was stirred for about two hours. Water/2N hydrochloric acid (1/1) was added, the aqueous phase was extracted with ethyl acetate, the organic phases were washed with water and dried and the solvent was distilled off, and the residue was then purified by column chromatography (mobile phase petroleum ether/ethyl acetate 85/5). 1.5 g of the title compound were isolated as a violet viscous oil.

Workup

temperaturethe reaction mixture was heated
temperatureat reflux temperature for about 40 min
extractionthe aqueous phase was extracted with ethyl acetate
washthe organic phases were washed with water
customdried
distillationthe solvent was distilled off
customthe residue was then purified by column chromatography (mobile phase petroleum ether/ethyl acetate 85/5)

Sources & evidence

ORD record: ord-9cadd0e38ce64128bee78903c376aa78
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06767923B2

Reaction notes

Loading…