Methanol → 1,3,5-Benzenetrimethanol
Reaction equation
[C:1]1([C:15](OC)=[O:16])[CH:6]=[C:5]([C:7](OC)=[O:8])[CH:4]=[C:3]([C:11](OC)=[O:12])[CH:2]=1.CO>C1COCC1>[OH:8][CH2:7][C:5]1[CH:4]=[C:3]([CH2:11][OH:12])[CH:2]=[C:1]([CH2:15][OH:16])[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a stirring solution of trimethyl 1,3,5-benzenetricarboxylate (10.45 g, 41.4 mmol) in 70 ml of anhydrous THF is added at room temperature a 10M solution of borane-methyl sulfide complex (25 ml, 248 mmol) and the solution is heated to reflux for 3 h. The mixture is then added slowly to 50 ml of MeOH and the resulting mixture is heated at 70° C. for 10 min to remove the methyl sulfide. Evaporation of solvent, washing twice with 50 ml of MeOH and evaporation of MeOH gives 1,3,5-tris(hydroxymethyl)benzene (6.96 g, 100%). 1H NMR (D2O): δ 4.52 (6H, s), 7.15 (3H, s).
Workup
- temperaturethe solution is heated
- temperatureto reflux for 3 h
- customto remove the methyl sulfide
- customEvaporation of solvent
- washwashing twice with 50 ml of MeOH and evaporation of MeOH
Sources & evidence
- ORD record
- ord-13ed01a7000e44dca15eefeecd62cf81
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121253
Reaction notes
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