Acetic Anhydride → HCID 12899886, compound
Reaction equation
[F:1][CH2:2][C:3]([CH2:21][F:22])([CH3:20])[CH:4]([OH:19])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[N:9][CH:8]=[N:7]1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([O:19][CH:4]([C:3]([CH2:21][F:22])([CH2:2][F:1])[CH3:20])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[N:9][CH:8]=[N:7]1)(=[O:25])[CH3:24]Participants
Conditions
- Temperature
- 100 °C
Procedure
112 g (0.328 mol) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-ol (as the diastereomeric mixture of the pure forms A and B) were dissolved in 500 ml of acetic anhydride. The solution was stirred at 100° C. for 16 hours, the excess acetic anhydride was distilled off in vacuo and the residue was taken up in 600 ml of methylene chloride. The organic phase was washed twice with 1.5 liters of water each time, dried over sodium sulphate and concentrated. The oily residue was subjected to fractional crystallization in diisopropyl ether. 48 g (38% of theory) of the A-form (Compound 1a) of 2-acetoxy-3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butane of melting point 130°-133° C. and 20.5 g (16% of theory) of the B-form (Compound 1b) of 2-acetoxy-3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butane of melting point 98° C. were obtained.
Workup
- distillationthe excess acetic anhydride was distilled off in vacuo
- washThe organic phase was washed twice with 1.5 liters of water each time
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- customThe oily residue was subjected to fractional crystallization in diisopropyl ether
Sources & evidence
- ORD record
- ord-927c1fe99516406b85d0b802728066c9
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04359470
Reaction notes
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