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

HRID 1613315
Notes
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Reaction equation

HRID 1613315 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 that 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 that mixture had been dried
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ef0254ff95154186a9c7de4f73e8f051
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05192766

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes