Ammonia → 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethyl-1,4-butanedione

HRID 845255Notes

Reaction equation

N.[Na].[CH3:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=[O:6].[Cl-].[NH4+]>C(Cl)Cl>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[O:13][CH3:14])[C:5]([CH:4]([CH:4]([C:5](=[O:6])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH3:3])[CH3:3])=[O:6]

Participants

Conditions

Temperature: -40 °C

Procedure

To 100 ml of liquid NH3 and 100 mg FeCl3, 1 g of sodium was added and stirred for 1 hr at -40° C. To that 7.7 g of 3,4-dimethoxypropiophenone was added and stirred for 1/2 hr. Eleven g of α-bromo-3,4-dimethoxypropiophenone was then added and stirring continued for 11/2 hrs. At this point, 11 g of ammonium chloride and 200 ml of methylene chloride was added and the temperature allowed to rise to room temperature. Filtration, evaporation and crystalization of the residue from methanol gave 14.5 g of racemic-2,3-bis(3,4-dimethoxybenzoyl)butane as a white solid. NMR (CDCl3) δ1.32(6H, d, J=7Hz), 3.92 and 3.94 (6H each, s, OCH3, 6.8-7.8 (6H, ArH); m.p. 141°-142° C.

Workup

stirringstirred for 1/2 hr
stirringstirring
custom2 hrs
customto rise to room temperature
filtrationFiltration, evaporation and crystalization of the residue from methanol

Sources & evidence

ORD record: ord-62e062ef8a7e4c1489bb9c4ed7da88e7
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04757084

Reaction notes

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