Sulfuric Acid → 3-(3',4'-Dichloro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

HRID 26909Notes

Reaction equation

HRID 26909 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[CH:13][CH:12]=1)(=[O:10])[CH3:9].S(=O)(=O)(O)O>[Zn].C1C=CC=CC=1>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[CH:13][CH:12]=1)([OH:10])[CH3:9])[CH3:7]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 167688151-[4-(3,4-Dichlorophenyl)phenyl]ethan-1-one

Product 1

HCID 544122843-(3',4'-Dichloro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 20 g. of ethyl bromoacetate, 26.5 g. of 4-acetyl-3',4'-dichlorobiphenyl and 8 g. of zinc foil is added to 100 ml. of benzene and the mixture is stirred and heated under reflux for one hour. It is cooled and dilute sulfuric acid is added to decompose the alcoholate obtained. The organic phase is separated off and, after the customary work up, 3-(3',4'-dichloro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester is obtained.

Workup

  1. additionA mixture of 20 g
  2. temperatureheated
  3. temperatureunder reflux for one hour
  4. temperatureIt is cooled
  5. customobtained
  6. customThe organic phase is separated off

Sources & evidence

ORD record
ord-4e1f0da971e1426899736fcb4ac4bc66
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Reaction notes

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