Sulfuric Acid → (5-Bromo-2-methylphenyl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:18])=[C:12]([CH:17]=1)[C:13](OC)=[O:14].C(OCC)(=O)C.S(=O)(=O)(O)O>C(OCC)C.O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:18])=[C:12]([CH:17]=1)[CH2:13][OH:14]Participants
Procedure
To a suspension of 4.2 g (0.1094 mol) of lithium aluminum hydride in 250 ml of dry diethyl ether was added dropwise a solution of 33.4 g (0.1458 mol) of methyl 5-bromo-2-methylbenzoate in 50 ml of dry diethyl ether at room temperature over 30 minutes with ice-cooling under an atmosphere of nitrogen. The mixture was stirred at room temperature for 2 hours. About 10 ml of ethyl acetate was added dropwise thereto and further about 50 ml of tetrahydrofuran was added thereto. The mixture was added to 200 ml of a 10% aqueous solution of sulfuric acid and ice, and the mixture was separated. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried and concentrated. The residue (28.7 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=10:1 and then 5:1) to obtain 24.36 g of 5-bromo-2-methylbenzylalcohol as crystals.
Workup
- temperaturecooling under an atmosphere of nitrogen
- customthe mixture was separated
- washThe organic layer was washed successively with water
- dry with materiala saturated aqueous solution of sodium bicarbonate and saturated brine, then dried
- concentrationconcentrated
- washeluted with n-hexane
Sources & evidence
- ORD record
- ord-349d6a2c4cfc437daacbc4b8139de61b
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06489487B1
Reaction notes
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