Ammonium Chloride → 1-(2,3-Dichlorophenyl)ethanol
Reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl-].[NH4+].[CH:13]1C=CC=CC=1.C(OCC)C>>[CH3:13][CH:4]([OH:5])[C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=1[Cl:1]Participants
Procedure
Iodomethane (324.89 g, 2.288 mol) was added dropwise, with stirring, to magnesium turnings (54.88 g, 2.288 mol) in dry ether (1 liter), to form methyl magnesium iodide. 2,3-Dichlorobenzaldehyde (200 g, 1.144 mol) dissolved in benzene/diethyl ether (1 liter, 50:50) solution was added dropwise, with stirring, to the Grignard. The reaction mixture was allowed to stir at room temperature overnight. The solution was refluxed for 2 hours, and then allowed to cool. The reaction mixture was poured into saturated ammonium chloride solution (5 liters) and the organic layer separated. The aqueous layer was extracted with ether (3×2 liters). The organic phases were combined, washed with brine (1×2 liters), dried over anhydrous magnesium sulphate, filtered and evaporated down. α-Methyl-2,3-dichlorobenzyl alcohol (196.4 g, 90% yield) was obtained as a yellow oil which crystallised on standing to give a pale-yellow solid. T.l.c. (SiO2 ;CHCl3) showed no impurities so no further purification was carried out. However, if necessary the alcohol nay be recrystallised from 40-60° C. petroleum ether to afford white prisms of melting point 53° C.
Workup
- additionwas added dropwise
- stirringto stir at room temperature overnight
- temperatureThe solution was refluxed for 2 hours
- temperatureto cool
- customthe organic layer separated
- extractionThe aqueous layer was extracted with ether (3×2 liters)
- washwashed with brine (1×2 liters)
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- customevaporated down
Sources & evidence
- ORD record
- ord-9a02a832e7d54075bcd885cd4cf1bf0b
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05925755
Reaction notes
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