1-(Phenylmethyl) butanedioate → Benzyl 4-chloro-4-oxobutanoate

HRID 1287336Notes

Reaction equation

HRID 1287336 reaction equation
[C:1]([CH2:11][CH2:12][C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)([Cl:18])=O>CN(C)C=O>[C:1]([CH2:11][CH2:12][C:13]([Cl:18])=[O:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 87881-(Phenylmethyl) butanedioateHCID 24386Thionyl Chloride

Product 1

HCID 12550027Benzyl 4-chloro-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5 grams of beta-carbobenzyloxypropionic acid (IV) in 50 ml. of thionyl chloride containing 0.5 ml of anhydrous dimethylformamide is allowed to stand, sheltered from moisture, for two days. The excess thionyl chloride is distilled off under a high vacuum, and the residue, which is a yellow oil, is heated in a flask to 110°C under an abs. pressure of 0.4 mmHg in order to strip the head fractions. The undistilled residue is taken up with ethyl ether, decolorized with charcoal, filtered and concentrated again. There are obtained about 3.48 grams (64% of theory) of (V) which is employed as such for the following stage.

Workup

  1. distillationThe excess thionyl chloride is distilled off under a high vacuum
  2. filtrationfiltered
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-efa53def9d56435fb20b44148a42909e
Source dataset
uspto-grants-1976_10
Patent number
US03984461

Reaction notes

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