4,4'-Dimethoxybenzophenone → Ethyl 3,3-bis(4-methoxyphenyl)-3-hydroxy-2-methylpropionate

HRID 2380706Notes

Reaction equation

HRID 2380706 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:9][O:10][C:11]1[CH:26]=[CH:25][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1>[Zn].C1C=CC=CC=1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]([C:14]2[CH:25]=[CH:26][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)([OH:16])[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 70324,4'-DimethoxybenzophenoneHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 19421607Ethyl 3,3-bis(4-methoxyphenyl)-3-hydroxy-2-methylpropionateYield 50.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 8.25 g of ethyl 2-bromopropionate, 11.81 g of 4,4'-dimethoxybenzophenone, 7.16 g of zinc and 70 ml of benzene was heated on an oil bath for 4 hours under reflux. The mixture was then allowed to stand to cool, after which the reaction solution was filtered. The filtrate was washed with 10% w/v aqueous sulfuric acid, with water and with a saturated aqueous solution of sodium chloride, in that order. After the mixture had been dried, the solvent was distilled off under reduced pressure. The residue was subjected to flash column chromatography through silica gel (about 400 mesh, 300 g). 7.92 g of the title compound were obtained as white crystals, melting at 67°-69° C. (after recrystallisation from a mixture of methylene chloride and hexane), from those fractions eluted with a 100:2 by volume mixture of hexane and ethyl acetate.

Workup

  1. temperaturewas heated on an oil bath for 4 hours
  2. temperatureunder reflux
  3. temperatureto cool
  4. filtrationafter which the reaction solution was filtered
  5. washThe filtrate was washed with 10% w/v aqueous sulfuric acid, with water and with a saturated aqueous solution of sodium chloride, in that order
  6. customAfter the mixture had been dried
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7848ba49939f414896ec6d4724e40e32
Source dataset
uspto-grants-1994_11
Patent number
US05369106

Reaction notes

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