2-Methylbenzenesulfonic acid → 3-Furancarboxylic acid, 2-methyl-4-(trifluoromethyl)-, ethyl ester

HRID 1654109Notes

Reaction equation

HRID 1654109 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][C:5](O)([C:12]([F:15])([F:14])[F:13])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:12]([F:14])([F:15])[F:13])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21819745HCID 21819745, compound

Product 1

HCID 120093303-Furancarboxylic acid, 2-methyl-4-(trifluoromethyl)-, ethyl esterYield 75.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g of the product of Stage A were heated for 7 hours at reflux in 50 ml of toluene in the presence of 0.5 g of toluenesulfonic acid and the mixture was allowed to return to room temperature. The solvent was evaporated and the residue was chromatographed on silica (eluent: 95/5 n-hexane/ethyl acetate) to obtain 6.95 g of the expected product.

Workup

  1. customto return to room temperature
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed on silica (eluent: 95/5 n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5d03d18f87ea40f59f3aa2279892f7b1
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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