Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate → 2-Methyl-3-(4-methylphenyl)-2-propen-1-ol
Reaction equation
[CH3:1][C:2](=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3](OCC)=[O:4]>C1(C)C=CC=CC=1>[CH3:1][C:2](=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[CH2:3][OH:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 3.5 °C
Procedure
To a solution of ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate (1002 g) in toluene (5371 ml) was added dropwise a 70% solution of dihydrobis(2-methoxyethoxy) sodium aluminate in toluene (2152 g) at 10° C. or below. The solution was stirred at 2 to 5° C. for 1 hr, a 10% solution of Rochel's salt (5968 ml) was added dropwise thereto at 20° C. or below and the solution was stirred at room temperature for 30 min. The toluene layer was fractionated, and washed with a 10% solution of Rochel's salt (2984 ml) and then washed with water. The solvent was distilled off to give the title compound as an oil (756 g, yield 93.9%).
Workup
- stirringat 20° C. or below and the solution was stirred at room temperature for 30 min
- washwashed with a 10% solution of Rochel's salt (2984 ml)
- washwashed with water
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-fa4bf5071d6f4b9a93665f6d04784d45
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420070B2
Reaction notes
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