Allyl chloroformate → HCID 22915101, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14]>[OH-].[Na+]>[CH2:16]([O:15][C:13]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)=[O:14])[CH:17]=[CH2:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7.55 g of 4-(aminomethyl)-benzoic acid in 50 ml of 1N sodium hydroxide solution were added at 6°-8° C. over 1.5 h 6.55 g of allyl chloroformate. Stirring was continued at 0° C. for 0.5 h and the mixture was then extracted with 60 ml of diethyl ether. The organic phase was extracted with 20 ml of saturated sodium carbonate solution and the combined aqueous layers were then acidified to pH 1.8 by the addition of 12N sulfuric acid and subsequently extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over sodium sulfate, and the solvent was evaporated in vacuo. The solid residue was crystallized from ethyl acetate/hexane to yield 7.61 g of 4-(allyloxycarbonylaminomethyl)-benzoic acid as a white solid, m.p. 175°-177° C.
Workup
- extractionthe mixture was then extracted with 60 ml of diethyl ether
- extractionThe organic phase was extracted with 20 ml of saturated sodium carbonate solution
- additionthe combined aqueous layers were then acidified to pH 1.8 by the addition of 12N sulfuric acid
- extractionsubsequently extracted with ethyl acetate
- extractionThe ethyl acetate extract
- washwas washed with brine
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated in vacuo
- customThe solid residue was crystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-639cce0405f349069c35c2655b7409db
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05589473
Reaction notes
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