Benzaldehyde → 2-(2-Hydroxy-2-phenylethyl)-3,5,6-trimethylpyrazine
Reaction equation
C1([Li])C=CC=CC=1.[CH3:8][C:9]1[N:14]=[C:13]([CH3:15])[C:12]([CH3:16])=[N:11][C:10]=1[CH3:17].[CH:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CCOCC>[OH:25][CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][C:10]1[C:9]([CH3:8])=[N:14][C:13]([CH3:15])=[C:12]([CH3:16])[N:11]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of phenyllithium in benzene-ether (90 milliliters, 0.095 mole) was diluted with 100 milliliters anhydrous ether and cooled to 0° C. A solution of 13.6 grams tetramethylpyrazine (0.1 mole) in 50 milliliters ether was added slowly to the phenyllithium solution. The reaction mixture was stirred at room temperature for 2 hours and heated under reflux for 1 hour. The mixture was allowed to cool to room temperature and a solution of 10 grams of freshly distilled benzaldehyde (0.1 mole) in 50 milliliters of ether was added dropwise. The mixture was stirred at room temperature for an additional 1.5 hours and cooled to 0° C. Water was added, and the organic phase was separated and washed three times with water. The recovered water extracts were washed with methylene chloride.
Workup
- temperatureheated
- temperatureunder reflux for 1 hour
- temperatureto cool to room temperature
- stirringThe mixture was stirred at room temperature for an additional 1.5 hours
- temperaturecooled to 0° C
- customthe organic phase was separated
- washwashed three times with water
- washThe recovered water extracts were washed with methylene chloride
Sources & evidence
- ORD record
- ord-3997c429ec9e458fb0ee6a743cbde9bc
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04259969
Reaction notes
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