Phenylacetic Acid → HCID 2733559, compound
Reaction equation
C([Li])CCC.CCCCCC.C(NC(C)C)(C)C.[C:19]1([CH2:25][C:26]([OH:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:29][Si:30]([CH3:33])([CH3:32])Cl>O1CCCC1>[CH3:29][Si:30]([CH3:33])([CH3:32])[O:27][C:26]([O:28][Si:30]([CH3:33])([CH3:32])[CH3:29])=[CH:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of butyllithium in hexane (0.4 mol, 250 ml of 1.6 M solution) was added to a solution of 40 g (0.4 mol) of diisopropylamine in 300 ml of tetrahydrofuran cooled in an ice-bath. A solution of 27.23 g (0.2 mol) of benzeneacetic acid in 200 ml of tetrahydrofuran was added near 0° C. and the reaction mixture was stirred for 30 minutes at 0° C. A 100 g portion of trimethylchlorosilane was added, the mixture was warmed to room temperature, stirred for 1.5 hours, and then filtered under nitrogen. The filtrate was evaporated to dryness under reduced pressure; the residue was dissolved in 80 ml of diethyl ether and filtered. The filtrate was evaporated to dryness and then distilled to give 37.2 g of β,β-[bis(trimethylsiloxy]styrene as a colorless liquid: bp 95° C. (0.5 mm).
Workup
- temperaturecooled in an ice-bath
- temperaturethe mixture was warmed to room temperature
- stirringstirred for 1.5 hours
- filtrationfiltered under nitrogen
- customThe filtrate was evaporated to dryness under reduced pressure
- dissolutionthe residue was dissolved in 80 ml of diethyl ether
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- distillationdistilled
Sources & evidence
- ORD record
- ord-9d2cd30195f548859fcb04664ea84d83
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215044
Reaction notes
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