Benzene → HCID 53744655, compound

HRID 2072224Notes

Reaction equation

HRID 2072224 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)=[O:3].[CH2:17]([O:19][C:20](=[O:23])[CH2:21]Br)[CH3:18].C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:17]([O:19][C:20](=[O:23])[CH2:21][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([OH:3])[CH3:1])[CH3:18]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7748Ethyl bromoacetateHCID 2367834'-Phenoxyacetophenone

Product 1

HCID 53744655HCID 53744655, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

21.2 g. of 4-phenoxyacetophenone and 11.1 ml. of bromoacetic acid ethyl ester are dissolved in a mixture of 75 ml. of benzene and 75 ml. of toluene. 40 ml. of this solution are added to 7 g. of zinc powder (previously washed successively with 1% hydrochloric acid, water and acetone, and then dried) and the mixture is heated to 70° while stirring and passing in nitrogen. After the reaction has begun, the remainder of the solution is added dropwise, the mixture is boiled for one hour and cooled and 40 ml. of 20% sulfuric acid are added dropwise in order to decompose the resulting alcoholate of the formula C6H5O--p--C6H4 --C(CH3)--(OZnBr)--CH2 --COOC2H5. The organic phase is separated off and standard working up gives 3-p-phenoxyphenyl-3-hydroxy-butyric acid ethyl ester.

Workup

  1. additionof this solution are added to 7 g
  2. washof zinc powder (previously washed successively with 1% hydrochloric acid, water and acetone
  3. customdried) and the mixture
  4. temperatureis heated to 70°
  5. additionthe remainder of the solution is added dropwise
  6. temperaturecooled
  7. additionof 20% sulfuric acid are added dropwise in order
  8. customThe organic phase is separated off

Sources & evidence

ORD record
ord-8871cd4f1640497091000f7681dcc614
Source dataset
uspto-grants-1977_09
Patent number
US04049823

Reaction notes

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