Sodium hydride → Ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylpropionate

HRID 1105871

Reaction equation

HRID 1105871 reaction equation
[H-].[Na+].[OH:3][C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28][O:3][C:4]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:26][CH:25]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6429709Ethyl 2-hydroxy-2-phenylpropanoateHCID 127738464'-Chloro-4-chloromethylbiphenyl

Product 1

HCID 20555297Ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylpropionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.05 g., 50% w/w dispersion in mineral oil), was added to a stirred solution of ethyl 2-hydroxy-2-phenylpropionate (3.48 g.) at 4° C. in dimethylformamide (100 ml.). After 1 hour, 4-(4-chlorophenyl)benzyl chloride (4.74 g.) was added and stirring was continued at 4° C. for 1 hour and then at room temperature for 20 hours. The mixture was neutralised by cautious addition of N-hydrochloric acid and then extracted with ether. The extracts were washed with water, dried (MgSO4) and evaporated to give ethyl 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylpropionate as an oil (7.9 g.).

Workup

  1. waitwas continued at 4° C. for 1 hour
  2. waitat room temperature for 20 hours
  3. extractionextracted with ether
  4. washThe extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-132b3d2b66134e188776e7452ed77ac8
Source dataset
uspto-grants-1982_01
Patent number
US04310544

Linked notes

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