Water → 2,3-Dimethylpent-3-yl allyl carbonate
Reaction equation
[CH3:1][CH:2]([C:4]([CH3:8])([OH:7])[CH2:5][CH3:6])[CH3:3].C[Li].Cl[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13].O>O1CCCC1.C(OCC)C>[C:12](=[O:13])([O:14][CH2:15][CH:16]=[CH2:17])[O:7][C:4]([CH3:8])([CH2:5][CH3:6])[CH:2]([CH3:3])[CH3:1]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 11.62 grams (0.1 mole) of 2,3-dimethylpentan-3-ol in 75 milliliters of anhydrous tetrahydrofuran at 0° C was added one equivalent of methyllithium in diethyl ether, followed by 12.1 grams (0.10 mole) of allyl chloroformate in 25 milliliters of anhydrous tetrahydrofuran. During both additions the temperature was maintained at 0° C. After the last addition was complete the reaction mixture was stirred for about 18 hours and allowed to warm to ambient temperature. The reaction mixture was poured into water, and then extracted with ether. The ether solution was washed four times with water and dried over magnesium sulfate. Removal of solvent under reduced pressure yielded 18.27 grams (93.1% crude yield) of a yellow oil. Vacuum distillation gave 10.79 grams of 2,3-dimethylpent-3-yl allyl carbonate, b.p. 59°-60° C/0.15 mm.
Workup
- additionAfter the last addition
- temperatureto warm to ambient temperature
- extractionextracted with ether
- washThe ether solution was washed four times with water
- dry with materialdried over magnesium sulfate
- customRemoval of solvent under reduced pressure
- customyielded 18.27 grams (93.1% crude yield) of a yellow oil
- distillationVacuum distillation
Sources & evidence
- ORD record
- ord-ab4cdb8115e948d8b76618b248b2a44c
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04092988
Reaction notes
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