2,2,4-Trimethyl-1,3-pentanediol → 3-Pentanol, 2,2,4-trimethyl-1-[(2-methyl-2-propen-1-yl)oxy]-

Temperature

100 °C

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.

1. customTo a 1 L flask equipped with a reflux condenser
2. temperatureThis mixture was heated in an oil bath
3. customreached 50° C.
4. additionDuring the addition
5. temperatureThe reaction mixture was cooled
6. customquenched with 400 ml of water
7. extractionextracted twice with 100 ml of toluene
8. washThe combined organic layers were washed with 50 ml of saturated ammonium chloride and 50 ml of saturated sodium chloride
9. customevaporated

ORD record

ord-b93164d19668495195d8b6e481c150c9

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132391B2