Potassium Hydroxide → 1-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

HRID 1602399Notes

Reaction equation

HRID 1602399 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[OH-].[K+].[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15]Br>CS(C)=O.O>[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 27373944-Fluoro-3-methylphenol

Product 1

HCID 196116591-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-fluoro-3-methylphenol (36.7 g), potassium hydroxide pellets (19.5 g) and bromoacetaldehyde dimethyl acetal (34.6 ml) in dimethyl sulphoxide (240 ml) was heated at 110° for 24 h. The mixture was cooled, diluted with water (350 ml) and extracted with hexane. Evaporation of the extracts gave the title compound as an oil (52.3 g).

Workup

  1. temperaturewas heated at 110° for 24 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with hexane
  4. customEvaporation of the extracts

Sources & evidence

ORD record
ord-97012483233c4b518f4a00abe00edd50
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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