p-Toluenesulfonic acid → 1-Dimethoxymethyl-2-fluoro-4-trifluoromethyl-benzene

HRID 2111741Notes

Reaction equation

HRID 2111741 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1C=O.[CH:14](OC)([O:17][CH3:18])[O:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:16][O:15][CH:14]([O:17][CH3:18])[C:3]1[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[F:1]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 231124321-Dimethoxymethyl-2-fluoro-4-trifluoromethyl-benzeneYield 98%

Procedure

A solution of 2-fluoro-4-trifluoromethylbenzaldehyde (10.0 g, 52.0 mmol), trimethyl orthoformate (55.0 g, 520 mmol) and a catalytic amount of p-toluene sulfonic acid (5 mol %) was stirred at room temperature for 24 hours. The resulting solution was saturated with the addition of solid Na2CO3 and stirred for 15 minutes. The mixture was then filtered and the solution was evaporated. The residue was diluted with ether and evaporated yielding 12.1 g (98%) of the desired product as an oil.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe solution was evaporated
  3. additionThe residue was diluted with ether
  4. customevaporated

Sources & evidence

ORD record
ord-ccac143c54fa428e8258a46c9f9f8d4b
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

Loading…