Ethylene Oxide → 1-(2,2-Dimethoxyethoxy)-4-(2-ethoxyethyl)-2,3-dimethylbenzene

HRID 1086660Notes

Reaction equation

HRID 1086660 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([O:13][CH3:14])[O:11][CH3:12])=[C:4]([CH3:15])[C:3]=1[CH3:16].[Mg].C1OC1.[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH3:12][O:11][CH:10]([O:13][CH3:14])[CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:23][CH2:22][O:21][CH2:25][CH3:24])=[C:3]([CH3:16])[C:4]=1[CH3:15]

Participants

5

Reactant 4

HCID 6354Ethylene OxideHCID 8028TetrahydrofuranHCID 5462224MagnesiumHCID 147515551-Bromo-4-(2,2-dimethoxyethoxy)-2,3-dimethylbenzene

Product 1

HCID 147712621-(2,2-Dimethoxyethoxy)-4-(2-ethoxyethyl)-2,3-dimethylbenzene

Procedure

Grignard reaction was carried out in conventional manner from 5.0 g of 4-bromo-1-(2,2-dimethoxyethoxy)-2,3dimethylbenzene and 0.5 g of magnesium in 30 ml of tetrahydrofuran, and then 1.0 g of ethylene oxide was blown into the reaction mixture at 50° C. Further, the mixture was stirred at the same temperature for 2 hours. Tetrahydrofuran was removed under reduced pressure, and 50 ml of toluene and 50 ml of 1 N hydrochloric acid were added. The organic layer separated was washed with water, and then 5 ml of 20% sodium hydroxide, 4.0 g of diethylsulfate and 0.3 g of tetrabutylammonium chloride were added, followed by heating and stirring at 40° C. for 5 hours. After cooling, the toluene layer was washed with water, dried and then concentrated under reduced pressure The residual oil was purified by column chromatography (Wako Gel C-200, eluant: n-hexane ethyl acetate=10:1) to obtain 3.5 g of the title product.

Workup

  1. customGrignard reaction
  2. customwas blown into the reaction mixture at 50° C
  3. customTetrahydrofuran was removed under reduced pressure, and 50 ml of toluene and 50 ml of 1 N hydrochloric acid
  4. additionwere added
  5. customThe organic layer separated
  6. washwas washed with water
  7. addition5 ml of 20% sodium hydroxide, 4.0 g of diethylsulfate and 0.3 g of tetrabutylammonium chloride were added
  8. temperatureby heating
  9. stirringstirring at 40° C. for 5 hours
  10. temperatureAfter cooling
  11. washthe toluene layer was washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure The residual oil
  14. customwas purified by column chromatography (Wako Gel C-200, eluant: n-hexane ethyl acetate=10:1)

Sources & evidence

ORD record
ord-90f05fd72ed44cf59c2a321e91e0c2b0
Source dataset
uspto-grants-1991_07
Patent number
US05030755

Reaction notes

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