Toluene → 2-Methyl-4-phenyl-2-butanol
Reaction equation
[CH3:1][C:2]1([O:5][CH2:4]1)[CH3:3].[Cl-].[NH4+].[C:8]1([CH3:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Cu]I>[CH3:1][C:2]([OH:5])([CH2:4][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:3]Participants
Conditions
- Temperature
- -10 °C
Procedure
13.92 g of copper(I) iodide were added to the supernatant obtained according to example 1, and the flask was cooled to −10° C. Then, 52.70 g of isobutylene oxide were added gradually over a period of 1 hour using a dropping funnel, and the temperature was maintained between −10° C. and −6° C. A mild exotherm was observed during this latter process. After stirring the mixture for a further 2 hours at 0° C., a sample was taken for analysis by gas chromatography. This sample was worked up with ammonium chloride solution. The reaction mixture was worked up by addition of 400 ml of saturated ammonium chloride solution, and 200 ml of toluene were added. The organic phase was separated off and washed twice with 400 ml each time of saturated ammonium chloride solution. After drying over magnesium sulfate, the product was obtained by distillation in vacuo with a purity of >97%. A total of 88.9 g of 2-methyl-4-phenylbutan-2-ol were obtained, corresponding to a yield of 74%.
Workup
- customobtained
- temperaturethe temperature was maintained between −10° C. and −6° C
- additionwere added
- customThe organic phase was separated off
- washwashed twice with 400 ml each time of saturated ammonium chloride solution
- dry with materialAfter drying over magnesium sulfate
- customthe product was obtained by distillation in vacuo with a purity of >97%
Sources & evidence
- ORD record
- ord-4162ef62fadd451bbd0b21e5f69e0f64
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993812B2
Reaction notes
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