Reaction #806259

Reaction equation

2,2,4-trimethylpentan-1,3-diol

NaOH

methallyl chloride

→

1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol

Yield 101.8%

Conditions

Workup

1. 1
   OtherTo a 1 L flask equipped with a reflux condenser
2. 2
   TemperatureThis mixture was heated in an oil bath
3. 3
   Otherreached 50° C.
4. 4
   workup.ADDITIONDuring the addition
5. 5
   TemperatureThe reaction mixture was cooled
6. 6
   Otherquenched with 400 ml of water
7. 7
   Extractionextracted twice with 100 ml of toluene
8. 8
   WashThe combined organic layers were washed with 50 ml of saturated ammonium chloride and 50 ml of saturated sodium chloride
9. 9
   Otherevaporated

Procedure

To a 1 L flask equipped with a reflux condenser and a thermometer, was added 292.5 g (2.0 mol) of 2,2,4-trimethylpentan-1,3-diol, 352.0 g (4.4 mol) of 50% aqueous NaOH, and 6.45 g (20 mmol) of tetrabutyl ammonium bromide. This mixture was heated in an oil bath and when the reaction mixture reached 50° C., 199.2 g (2.2 mol) of methallyl chloride was added drop-wise over 50 minutes. During the addition, the oil bath temperature was gradually raised to 100° C. and the reaction was continued for an additional 3 hours at 100° C. The reaction mixture was cooled, quenched with 400 ml of water, and extracted twice with 100 ml of toluene. The combined organic layers were washed with 50 ml of saturated ammonium chloride and 50 ml of saturated sodium chloride and evaporated to give 408 g of crude 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol. After reduced pressure distillation (71–80° C., 3 mmHg), 377.1 g (yield 94.1%) of 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol was obtained.

Source