p-Toluenesulfonic acid → 1-(Dimethoxymethyl)-2-fluorobenzene

HRID 1249211Notes

Reaction equation

HRID 1249211 reaction equation
[F:1][C:2]1C=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[CH3:10][O:11][C:12]([O:15][CH3:16])(C)[CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[CH3:10][O:11][CH:12]([O:15][CH3:16])[C:13]1[CH:8]=[CH:7][CH:6]=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 114267321-(Dimethoxymethyl)-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.2 g of 2-fluorobenzaldehyde, 15 ml of 2,2-dimethoxypropane and 0.1 g of 4-toluenesulphonic acid was stirred at room temperature. After 24 hours, diethyl ether was added and the resultant solution washed with saturated sodium bicarbonate solution. Drying and evaporation of the organic phase gave the crude acetal. Distillation under vacuum at 90°-95° C./0.08 mm yielded the title compound as a colourless oil.

Workup

  1. washthe resultant solution washed with saturated sodium bicarbonate solution
  2. customDrying
  3. customevaporation of the organic phase
  4. customgave the crude acetal
  5. distillationDistillation under vacuum at 90°-95° C./0.08 mm

Sources & evidence

ORD record
ord-97a43d6db0e847688358fe9bece11458
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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