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

HRID 2421804Notes

Reaction equation

HRID 2421804 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([Cl:18])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 87881-(Phenylmethyl) butanedioateHCID 24386Thionyl Chloride

Product 1

HCID 12550027Benzyl 4-chloro-4-oxobutanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

4-(benzyloxy)-4-oxobutanoic acid (6.16 g, 1 eq, from Example 1a) was dissolved in toluene (20 mL) and placed in a 300 mL round bottom flask, fitted with a condenser. While the reaction was stirred under inert atmosphere, thionyl chloride (5.30 g, 1.5 eq) was added. A few drops of DMF were also added and tire reaction mixture was heated to 35° C. for 45 minutes and then to 60° C. for 2 hours. The solution was concentrated to 6.71 g of brownish oil.

Workup

  1. customplaced in a 300 mL round bottom flask
  2. customfitted with a condenser
  3. additionwas added
  4. customtire reaction mixture
  5. concentrationThe solution was concentrated to 6.71 g of brownish oil

Sources & evidence

ORD record
ord-843be3c062564c02808678a1a6469df9
Source dataset
uspto-grants-2011_06
Patent number
US07959958B2

Reaction notes

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