4-Chloro-3-methylphenol → HCID 12661867, compound

HRID 1602388Notes

Reaction equation

HRID 1602388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11].[OH-].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][CH:13]([O:16][CH2:17][CH3:18])[O:12][CH2:10][CH3:11])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 17324-Chloro-3-methylphenolHCID 14797Potassium HydroxideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 12661867HCID 12661867, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-chloro-3-methylphenol (47 g), bromoacetaldehyde diethyl acetal (45 ml) and potassium hydroxide (33.6 g) in dimethyl sulphoxide (250 ml) was heated at 120° for 2 h. The cooled mixture was partitioned between water (750 ml) and toluene (3×500 ml) and the combined organic extracts washed with brine/water 1:1 (3×300 ml) and dried (Na2SO4). The solvent was evaporated to give the title compound as a pale yellow oil (67.9 g)

Workup

  1. temperaturewas heated at 120° for 2 h
  2. customThe cooled mixture was partitioned between water (750 ml) and toluene (3×500 ml)
  3. washthe combined organic extracts washed with brine/water 1:1 (3×300 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8b4dbf893a6947a8ba3ffb115d7a79c3
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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