Ethanol → HCID 19421579, compound

HRID 2380708Notes

Reaction equation

HRID 2380708 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10][C:11]([O:13]CC)=[O:12])=[CH:5][CH:4]=1.[OH-].[Na+].[CH2:26](O)C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[C:10]([CH3:26])[C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 9818226HCID 9818226, compound

Product 1

HCID 19421579HCID 19421579, compound

Procedure

A mixture of 6.019 g of ethyl 3,3-bis(4-methoxyphenyl)acrylate (prepared as described in Preparation 107), 120 ml of ethanol and 80 ml of a 10% w/v aqueous solution of sodium hydroxide was stirred for 14 hours at room temperature. At the end of this time, the reaction mixture was heated on an oil bath at 100° C. for 4 hours, and then ethanol was distilled off. The residue was diluted with ice-water and washed with ethyl acetate. Concentrated hydrochloric acid was dropped onto the aqueous phase on an ice bath, to adjust the pH to a value of 2. The aqueous phase was extracted twice with methylene chloride. The combined methylene chloride extracts were washed with water, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure, to afford 5.117 g of the title compound as white crystals, melting at 134°-135° C. (after recrystallisation from a mixture of methylene chloride and hexane).

Workup

  1. temperatureAt the end of this time, the reaction mixture was heated on an oil bath at 100° C. for 4 hours
  2. distillationethanol was distilled off
  3. additionThe residue was diluted with ice-water
  4. washwashed with ethyl acetate
  5. additionConcentrated hydrochloric acid was dropped onto the aqueous phase on an ice bath
  6. extractionThe aqueous phase was extracted twice with methylene chloride
  7. washThe combined methylene chloride extracts were washed with water
  8. dry with materialdried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-c64fcc08ce0941eba7a57295703a0c86
Source dataset
uspto-grants-1994_11
Patent number
US05369106

Reaction notes

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