Methanol → 3-Buten-2-ol, 1,1-dimethoxy-2-methyl-
Reaction equation
C1(C)C=CC=CC=1.[CH3:8][O:9][CH:10]([O:16][CH3:17])[C:11]([CH3:15])([OH:14])[CH:12]=[CH2:13].[CH3:18][O-:19].[Na+].[CH3:21][OH:22]>>[CH3:8][O:9][CH:10]([O:16][CH3:17])[C:11]([CH3:15])([OH:14])[CH:12]=[CH2:13].[CH3:8][O:9][CH:10]([O:16][CH3:17])[C:11]([CH3:15])([O:14][C:18]([O:22][CH3:21])=[O:19])[CH:12]=[CH2:13]Participants
Procedure
1,000 parts of toluene and 292 parts of 1,1-dimethoxy-2-methyl-2-hydroxy-3-butene are taken, 437 parts of a 30 percent strength solution of sodium methylate in methanol are then added slowly at from 90° to 100° C. and at the same time the methanol is distilled off, until the internal temperature reaches 107° C. 236 parts of methyl chlorocarbonate are subsequently added at 30° C. and stirring is continued for 8 hours. The mixture is then stirred with 500 parts of water, after which the organic phase is separated from the aqueous phase. Working up the organic phase by distillation gives, in addition to unconverted 1,1-dimethoxy-2-methyl-2-hydroxy-3-butene, 348 parts of 1,1-dimethoxy-2-methyl-2-(methoxycarbonyloxy)-3-butene, of boiling point/20 mm Hg=107°-110° C. The yield is 85% of theory.
Workup
- distillationis distilled off, until the internal temperature
- customreaches 107° C
- addition236 parts of methyl chlorocarbonate are subsequently added at 30° C.
- stirringThe mixture is then stirred with 500 parts of water
- customafter which the organic phase is separated from the aqueous phase
- distillationWorking up the organic phase by distillation
Sources & evidence
- ORD record
- ord-875e9273b4cb459393c46d46fddad19f
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04187227
Reaction notes
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