Water → 2,6-Diethyl-4-methylbenzyl alcohol
Reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH:5]=[O:6])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>C(OCC)C>[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5][OH:6])[CH3:2]Participants
Procedure
A solution of 35.5 g (201.4 mmol) of 2,6-diethyl-4-methylbenzaldehyde, dissolved in 80 ml of diethyl ether is added dropwise to a suspension of 2.10 g (55.4 mmol) of lithium aluminium hydride in 200 ml of diethyl ether. The mixture is then heated at reflux for another 1 h. After cooling, the mixture is hydrolyzed with water and 10% strength sulphuric acid, the phases are separated and the aqueous phase is extracted two more times with diethyl ether. Drying (magnesium sulphate), distillative removal of the solvent and chromatography of the resulting crude product on silica gel (ethyl acetate/hexane=30:70) gives 33.10 g (92%) of 2,6-diethyl-4-methylbenzyl alcohol in the form of colourless crystals of m.p. 71-72° C. 1H-NMR (400 MHz, CDCl3): δ=1.22 (t, 6H), 2.30 (s, 3H), 2.74 (q, 4H), 4.71 (s, 2H), 6.90 (s, 2H).
Workup
- temperatureThe mixture is then heated
- temperatureat reflux for another 1 h
- temperatureAfter cooling
- customthe phases are separated
- extractionthe aqueous phase is extracted two more times with diethyl ether
- customDrying
- custom(magnesium sulphate), distillative removal of the solvent and chromatography of the resulting crude product on silica gel (ethyl acetate/hexane=30:70)
Sources & evidence
- ORD record
- ord-78777e775d634ce1bb2c4aa1c76e2e94
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367873B2
Reaction notes
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