Water → 2-[1-(3-Chlorophenoxy)ethyl]benzyl alcohol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH:6]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11])[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH:6]([C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[CH2:10][OH:11])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of the crude methyl 2-[1-(3-chlorophenoxy)ethyl]benzoate described above (14.8 g) in THF (50 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (1.93 g) in THF (70 ml) cooled to 0°-5° C. Following the addition, the reaction mixture was stirred at about 0° C. for 30 minutes, then at room temperature for 2 hours. It was poured carefully into water and was extracted with ether. The extracts were washed successively with water (×2) and brine, then dried and concentrated to give 2-[1-(3-chlorophenoxy)ethyl]benzyl alcohol (11.72 g, 85% pure by GC) as a yellow oil.
Workup
- temperaturecooled to 0°-5° C
- additionthe addition
- waitat room temperature for 2 hours
- extractionwas extracted with ether
- washThe extracts were washed successively with water (×2) and brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2e651b130ed244cfa517792e63117326
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05021581
Reaction notes
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