1-Chloro-2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propane → HCID 14878972, compound

HRID 414498Notes

Reaction equation

HRID 414498 reaction equation
Cl[CH2:2][C:3]([CH3:22])([CH3:21])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1.[F:23]C1C=CC(COC(CC)=C)=CC=1OC1C=CC=CC=1>>[F:23][CH2:2][C:3]([CH3:22])([CH3:21])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 148789691-Chloro-2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propaneHCID 212810742-(4-Fluoro-3-phenoxybenzyloxy)-but-1-ene

Product 1

HCID 14878972HCID 14878972, compound

Procedure

A mixture of 2,2-dimethyl-3-(4-fluoro-3-phenoxybenzyloxy)propy-1-yl p-toluenesulphonate (2.5 g), potassium fluoride (0.8 g) and tetraethylene glycol (7 cm3) was heated at 160° C. (under a drying tube to exclude moisture) for 3 hours. The reaction mixture was allowed to cool and stood at the ambient temperature for 17 hours. The mixture was poured into water and the products extracted into diethyl ether (2×200 cm3). The combined organic extracts were washed with water and dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave an orange oil (1.5 g) which was passed through a short silica gel column using petroleum ether (boiling range 40°-60° C.) containing 10% by volume diethyl as eluent. Analysis of the resulting oil indicated 3 major components which were separated and isolated by high pressure liquid chromatography (eluting with hexane containing 1% by volume ethyl acetate). The first and third fractions were identified as 1-chloro-2,2-dimethyl-3-(4 -fluoro-3-phenoxybenzyloxy)propane (0.25 g--thought to have been formed owing to the presence of chloride ion contamination of the starting materials) and 2-(4-fluoro-3-phenoxybenzyloxy)-but-1-ene (an elimination by-product) respectively. The title compound (0.29 g) was obtained as the second eluted fraction; characterising data for this compound are given below:

Workup

  1. additioncontaining 10% by volume diethyl as eluent
  2. customwere separated
  3. customisolated by high pressure liquid chromatography (eluting with hexane containing 1% by volume ethyl acetate)
  4. customto have been formed

Sources & evidence

ORD record
ord-c69c3635a5af4706be1a51a22b81e344
Source dataset
uspto-grants-1988_12
Patent number
US04792563

Reaction notes

Loading…