Water → [1-(1,1-Dimethoxyethyl)propenyl]benzene
Reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH3:7][O:8][C:9]([O:19][CH3:20])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.O>O1CCCC1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:7][O:8][C:9]([C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:1][CH3:2])([O:19][CH3:20])[CH3:18]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
At 5° C., a solution of 2.5 g of potassium tert-butoxide in 25 ml of tetrahydrofuran (THF) was added dropwise to 8.2 g of ethyltriphenylphosphonium bromide dissolved in 50 ml of THF. The mixture was then stirred at 5° C. for about 10 min, and a solution of 3.9 g of 2,2-dimethoxy-1-phenylpropan-1-one from Example 1 in 10 ml of THF was added dropwise. The reaction mixture was stirred at 20 to 25° C. for 72 h and then admixed with about 300 ml of water and extracted with methyl tert-butyl ether (MTBE). The organic phases were washed with water, dried and freed of the solvent. Silica gel chromatography (MTBE/cyclohexane 1:10) of the residue gave 2.2 g of product as an isomer mixture which can be further reacted without purification.
Workup
- stirringThe reaction mixture was stirred at 20 to 25° C. for 72 h
- extractionextracted with methyl tert-butyl ether (MTBE)
- washThe organic phases were washed with water
- customdried
Sources & evidence
- ORD record
- ord-da84d8cf4ddc4e2a99c0cd9e871950b3
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329359B1
Reaction notes
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