Water → 3-Buten-2-ol, 2-methyl-, acetate
Reaction equation
[CH3:1][C:2]([OH:6])([CH:4]=[CH2:5])[CH3:3].C(N(CC)CC)C.[C:14](OC(=O)C)(=[O:16])[CH3:15].O>C(Cl)Cl>[C:14]([O:6][C:2]([CH3:3])([CH:4]=[CH2:5])[CH3:1])(=[O:16])[CH3:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 2-methyl-3-buten-2-ol (86.13 g, 1.0 mole), triethylamine (101.19 g, 1.3 mole), and 4-dimethylaminopropyridine (25.0 g, 0.2 mole) at 0° C. is added dropwise acetic anhydride (102.09 g, 1.15 mole) in CH2Cl2 (700 ml). The mixture is stirred at 0° C. for 5 hours and at room temperature overnight. Water is then added and the CH2CL2 layer separated. The aqueous layer is extracted with CH2Cl2 (3×300 ml) and the combined CH2Cl2 solution is washed with cold 1N HCl (300 ml), water (330 ml) and dried over anhydrous MgSO4. Distillation of the CH2Cl2 solution gives 2-methyl-3-buten-2-yl acetate (113.07 g), 88 percent, boiling point 59° C. (80 mm Hg).
Workup
- customthe CH2CL2 layer separated
- extractionThe aqueous layer is extracted with CH2Cl2 (3×300 ml)
- washthe combined CH2Cl2 solution is washed with cold 1N HCl (300 ml), water (330 ml)
- dry with materialdried over anhydrous MgSO4
- distillationDistillation of the CH2Cl2 solution
Sources & evidence
- ORD record
- ord-a0b4595405524576bd514fd58fc23d2c
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04667050
Reaction notes
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