Sulfuryl chloride → HCID 19992468, compound

HRID 345504Notes

Reaction equation

HRID 345504 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.S(Cl)([Cl:19])(=O)=O>ClCCl>[Cl:19][CH:5]([C:6](=[O:14])[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH2:4][C:3]([O:2][CH3:1])=[O:15]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 230774Methyl 4-(4-chlorophenyl)-4-oxobutanoate

Product 1

HCID 19992468HCID 19992468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 179 g (0.79 mole) of methyl-3-(4-chlorobenzoyl)propionate in 175 mL of dichloromethane was cooled to 0° and treated dropwise with 69.8 mL (117.3 g; 0.86 mole, d=1.68) of sulfuryl chloride. After the addition was complete, the cold bath was removed, and the reaction mixture was allowed to warm to room temperature while stirring overnight. The mixture was treated with 100 mL of water and basified cautiously with 50% sodium hydroxide. The layers were separated, the dichloromethane layer dried over magnesium sulfate and evaporated under reduced pressure (245.3 g). The residue was purified by vacuum distillation (135° C./0.3 mm) to obtain three fractions for a total of 198.6 g (96%).

Workup

  1. additionAfter the addition
  2. customthe cold bath was removed
  3. additionThe mixture was treated with 100 mL of water and basified cautiously with 50% sodium hydroxide
  4. customThe layers were separated
  5. dry with materialthe dichloromethane layer dried over magnesium sulfate
  6. customevaporated under reduced pressure (245.3 g)
  7. distillationThe residue was purified by vacuum distillation (135° C./0.3 mm)
  8. customto obtain three fractions for a total of 198.6 g (96%)

Sources & evidence

ORD record
ord-0a9e9c142d6b4389bc168c3d76ca0624
Source dataset
uspto-grants-1991_10
Patent number
US05057534

Reaction notes

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