Triethylamine → 3-Benzoylpropionic acid

HRID 268288Notes

Reaction equation

HRID 268288 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])[CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O>C(Cl)(Cl)Cl>[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:8])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27600024-(3-Methylphenyl)-4-oxobutyric acid

Product 1

HCID 728713-Benzoylpropionic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 24.5 g. 3-(m-toluoyl)propionic acid (0.10 mole) and 10.1 g. triethylamine (0.10 mole) in 250 ml. of chloroform cooled to 0°C., there is added dropwise 10.8 g. (0.10 mole) of ethyl chloroformate at such a rate that the critical temperature does not exceed 10°C. The reaction is stirred for 2 1/2 hours to obtain the mixed anhydride of 3-benzoylpropionic acid which is then treated with 3.1 g. of methylamine (0.10 mole) in 100 ml. of chloroform. The cooling apparatus is removed and the reaction is stirred for about 20 hours. The chloroform layer is then washed with 50 ml. of water, 100 ml. 1N hydrochloric acid, 100 ml. saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue is crystallized from methylene chloride/hexane to give 5-hydroxy-1-methyl-5-(m-tolyl) pyrrolidone; m.p. 128°-130°C.

Workup

  1. additionTo a mixture of 24.5 g
  2. additionthere is added dropwise 10.8 g
  3. customdoes not exceed 10°C

Sources & evidence

ORD record
ord-9367b0f00a714a3c9e0e20c71eadaee7
Source dataset
uspto-grants-1976_03
Patent number
US03947460

Reaction notes

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