Potassium Hydroxide → 3-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

A reaction vessel was charged with 11.6 g of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 15.2 g of 10% aqueous potassium hydroxide solution and 30 ml of methanol. After stirring at room temperature for 24 hours, the reaction mixture was concentrated. Water was poured into the concentrate, and the mixture was extracted twice with 150 ml of diethyl ether. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 7.41 g of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propanol (83% yield), m.p., 56.6° C.

1. concentrationthe reaction mixture was concentrated
2. additionWater was poured into the concentrate
3. extractionthe mixture was extracted twice with 150 ml of diethyl ether
4. washwashed with water
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated
7. customto give a crude product

ORD record

ord-0ddd1e5c57194519a207d6565d8a6df2

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06214835B1