Ethylene carbonate → 2-(7-Chlorodibenzofuran-3-oxy)-ethanol

HRID 615174Notes

Reaction equation

HRID 615174 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:21]=[CH:20][C:11]2[C:12]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:13]=3[O:14][C:10]=2[CH:9]=1.C1(=O)O[CH2:25][CH2:24][O:23]1>CN(C)C=O>[Cl:7][C:8]1[CH:21]=[CH:20][C:11]2[C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:25][CH2:24][OH:23])=[CH:15][C:13]=3[O:14][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 204294997-Chlorodibenzofuran-3-ol

Product 1

HCID 204295042-(7-Chlorodibenzofuran-3-oxy)-ethanolYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

83 g (0.6 mole) of potassium carbonate were added to a solution of 262 g (1.2 moles) of 7-chlorodibenzofuran-3-ol in 600 ml of dry dimethylformamide, and a solution of 212 g (2.55 moles) of ethylene carbonate in 300 ml of dimethylformamide was then added dropwise in the course of 90 minutes at 100° C. The mixture was stirred for 8 hours at 120° C. and was then filtered under suction at 100° C., and the filtrate was evaporated down. The residue was dissolved in 2.5 liters of ethyl acetate, the solution was washed with three times 300 ml of water, the organic layer was dried, decolorized with 10 g of animal charcoal and evaporated down to 500 ml, and the residue was cooled to 10° C. The precipitate was filtered off under suction, washed with 60 ml of methanol, 50 ml of ether and 200 ml of petroleum ether in succession at +5° C., and dried. 225 g (71.4% of theory) of 2-(7-chlorodibenzofuran-3-yloxy)-ethanol of melting point 118°-120° C. were obtained.

Workup

  1. filtrationwas then filtered under suction at 100° C.
  2. customthe filtrate was evaporated down
  3. dissolutionThe residue was dissolved in 2.5 liters of ethyl acetate
  4. washthe solution was washed with three times 300 ml of water
  5. customthe organic layer was dried
  6. customevaporated down to 500 ml
  7. temperaturethe residue was cooled to 10° C
  8. filtrationThe precipitate was filtered off under suction
  9. washwashed with 60 ml of methanol, 50 ml of ether and 200 ml of petroleum ether in succession at +5° C.
  10. customdried

Sources & evidence

ORD record
ord-08da8e7e9de84cadaa00079d05467cb0
Source dataset
uspto-grants-1985_02
Patent number
US04497819

Reaction notes

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