3-Chloro-1-propanol → Butanoic acid, 3-oxo-, 3-chloropropyl ester
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>C(N(CC)CC)C>[C:9]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:10])[CH2:8][C:7]([CH3:6])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
3-Chloropropanol (47.3 g, 0.50 mole) and a catalytic amount of triethylamine at 65° C. were treated dropwise with 42 g (0.50 mole) of diketene. After the addition was complete, the reaction was stirred at 65° C. for an additional hour. Distillation of the residue furnished 72.9 g (82%) of product as a clear liquid, b.p. 78°-85° C. at 150 mm. Additional Formula II intermediates can be prepared by modifications of the above examples which would be understood by one skilled in the art of organic chemical synthesis.
Workup
- additionAfter the addition
- distillationDistillation of the residue
Sources & evidence
- ORD record
- ord-c45cc3c97de04b46b2f3d62d1f2167c3
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04895846
Reaction notes
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