Water → Benzene, (2,2-dimethoxyethoxy)-

HRID 1249210Notes

Reaction equation

HRID 1249210 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 105897Benzene, (2,2-dimethoxyethoxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 31.3 g of phenol, 60.0 g of bromoacetaldehyde dimethyl acetal and 80 g of potassium carbonate was heated at 150° C. in 300 ml of dimethylformamide. After 4.5 hours the reaction mixture was cooled, added to water, and extracted with diethyl ether. Separation, drying and evaporation of the organic phase gave the crude product. Vacuum distillation, bp 88°-98° C./1 mm yielded the title compound as a colourless oil.

Workup

  1. temperatureAfter 4.5 hours the reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. customSeparation
  4. customdrying
  5. customevaporation of the organic phase
  6. customgave the crude product
  7. distillationVacuum distillation, bp 88°-98° C./1 mm

Sources & evidence

ORD record
ord-6edca12bbc14458b9812a7888a7ce692
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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