Water → HCID 69528391, compound
Reaction equation
[O:1]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][C:21]=1[Cl:34])[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>O1CCCC1>[Cl:34][C:21]1[CH:22]=[C:23]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:25][C:20]=1[CH2:19][OH:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-((tert-butyldiphenylsiloxy)methyl)-2-chloro-4-(phenoxymethyl)benzene (2.84 g) in tetrahydrofuran (14 ml) was added tetrabutyl ammonium fluoride/tetrahydrofuran solution (1.0 M, 7.0 ml) under ice-cooling and the mixture was stirred for 1.5 hr. Water was added to the reaction mixture and the resulting product was extracted twice with ethyl acetate. The organic layers were combined, washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give 2-chloro-4-(phenoxymethyl)benzyl alcohol (1.38 g) as a white powder.
Workup
- temperaturecooling
- extractionthe resulting product was extracted twice with ethyl acetate
- washwashed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-a6a4a6217fd44d35b8f4571d95eb711f
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07060721B1
Reaction notes
Loading…