Pyridine → 1-Chloro-2-(7-chlorodibenzofuran-3-oxy)-ethane

HRID 354689Notes

Reaction equation

N1C=CC=CC=1.[Cl:7][C:8]1[CH:24]=[CH:23][C:11]2[C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21]O)=[CH:15][C:13]=3[O:14][C:10]=2[CH:9]=1.S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[Cl:27][CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:12]2[C:11]3[CH:23]=[CH:24][C:8]([Cl:7])=[CH:9][C:10]=3[O:14][C:13]=2[CH:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

11.9 g (0.15 mole) of pyridine were added to a suspension of 26.2 g (0.1 mole) of 2-(7-chlorodibenzofuran-3-oxy)-ethanol in 100 ml of dry toluene, and 17.9 g (0.15 mole) of thionyl chloride were then added dropwise at 3°-15° C. The mixture was stirred for 1 day at 40° C. and for a further 8 hours at 70° C. and cooled, and 150 ml of toluene and 200 ml of ice-water were added. The organic layer was washed with 100 ml of water, 50 ml of hydrochloric acid and 50 ml of 1 N sodium hydroxide solution in succession and finally with 100 ml of water, and was dried and concentrated. The solid residue was stirred with 40 ml of petroleum ether at +3° C. (ice-bath) for 30 minutes, filtered off with suction, washed with a little cold petroleum ether and dried. 22.8 g of 1-chloro-2-(7-chlorodibenzofuran-3-oxy)-ethane were obtained as colorless crystals of melting point 105°-107° C.; yield: 81% of theory.

Workup

additionwere then added dropwise at 3°-15° C
temperaturecooled
washThe organic layer was washed with 100 ml of water, 50 ml of hydrochloric acid and 50 ml of 1 N sodium hydroxide solution in succession and finally with 100 ml of water
customwas dried
concentrationconcentrated
stirringThe solid residue was stirred with 40 ml of petroleum ether at +3° C. (ice-bath) for 30 minutes
filtrationfiltered off with suction
washwashed with a little cold petroleum ether
customdried

Sources & evidence

ORD record: ord-dd4ff5ac3863433085d68fa3863b849e
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04376776

Reaction notes

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