Water → 4-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene

HRID 1584769Notes

Reaction equation

HRID 1584769 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13]Br.[OH-].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH:12]([O:15][CH3:16])[O:11][CH3:10])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 168964-Bromo-2-methylphenolHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 196085464-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-bromo-2-methylphenol (5 g), bromoacetaldehyde dimethyl acetal (3.8 ml) and potassium hydroxide (3.0 g) in dimethylsulphoxide (15 ml) was heated to reflux for 21/2 h. Water (50 ml) was added to the cooled mixture which was then extracted with ether (4×50 ml). The extracts were washed with 5N sodium hydroxide (50 ml) and brine (50 ml), dried (MgSO4), then evaporated in vacuo to give the title compound as a brown oil (6 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 21/2 h
  3. extractionwas then extracted with ether (4×50 ml)
  4. washThe extracts were washed with 5N sodium hydroxide (50 ml) and brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c487d4ad6e6c49d5b10fa4e86605eb4f
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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