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

HRID 456554

Reaction equation

HRID 456554 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-498c52f8ffc045d89e1e78af52efdcf6
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Linked notes

Loading…