Water → HCID 23462498, compound

HRID 1395602Notes

Reaction equation

HRID 1395602 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[O:20]([C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[C:1]([CH2:9][CH2:10][C:11]([O:13][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 728713-Benzoylpropionic acidHCID 945441-(Bromomethyl)-3-phenoxybenzene

Product 1

HCID 23462498HCID 23462498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 12 g of 3-benzoylpropionic acid and 9.3 g of potassium carbonate in 100 ml of dimethylformamide (DMF), under nitrogen, is added m-phenoxybenzyl bromide (17.1 g). The reaction is stirred about 4 hr and then water added followed by extraction with ether. The combined extracts are washed with water, saturated sodium chloride, dried over calcium sulfate and rotoevaporated to give m-phenoxybenzyl 3-benzoylpropionate which can be further purified by prep. TLC eluting with 15% ethyl acetate/hexane.

Workup

  1. extractionfollowed by extraction with ether
  2. washThe combined extracts are washed with water, saturated sodium chloride
  3. dry with materialdried over calcium sulfate

Sources & evidence

ORD record
ord-4863baef19bd4f9289dbdeec63c34ac6
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

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