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

HRID 615175Notes

Reaction equation

HRID 615175 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

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 204295042-(7-Chlorodibenzofuran-3-oxy)-ethanol

Product 1

HCID 204295001-Chloro-2-(7-chlorodibenzofuran-3-oxy)-ethaneYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

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-yloxy)-ethanol in 100 ml of dry toluene, and 17.9 g (0.15 mole) of thionyl chloride were then added dropwise at from 3° to 15° C. The mixture was stirred for 1 day at 40° C. and for a further 8 hours at 70° C., after which it was 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, 50 ml of 1N sodium hydroxide solution and 100 ml of water in succession, and was dried and evaporated down. The solid residue was stirred for 30 minutes with 40 ml of petroleum ether at +3° C. (ice bath), and was then filtered off under suction, washed with a little cold petroleum ether and dried. 22.8 g (81% of theory) of 1-chloro-2-(7-chlorodibenzofuran-3-yloxy)-ethane were obtained at colorless crystals of melting point 105°-107° C.

Workup

  1. additionwere then added dropwise at from 3° to 15° C
  2. temperatureafter which it was cooled
  3. washThe organic layer was washed with 100 ml of water, 50 ml of hydrochloric acid, 50 ml of 1N sodium hydroxide solution and 100 ml of water in succession
  4. customwas dried
  5. customevaporated down
  6. stirringThe solid residue was stirred for 30 minutes with 40 ml of petroleum ether at +3° C. (ice bath)
  7. filtrationwas then filtered off under suction
  8. washwashed with a little cold petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-7f8b8468c0664c66a7a07e95df4b7083
Source dataset
uspto-grants-1985_02
Patent number
US04497819

Reaction notes

Loading…