2,6-Dimethylbenzoic acid → 2,6-Dimethyl-3-((2,2,2-trifluoroacetamido)methyl)benzoic acid

HRID 59353

Reaction equation

HRID 59353 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]([F:20])([F:19])[C:14]([NH:16][CH2:17]O)=[O:15]>OS(O)(=O)=O>[F:12][C:13]([F:20])([F:19])[C:14]([NH:16][CH2:17][C:10]1[C:2]([CH3:1])=[C:3]([C:7]([CH3:11])=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5])=[O:15]

Participants

4

Reactant 2

HCID 124392,6-Dimethylbenzoic acidHCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Product 1

HCID 866922272,6-Dimethyl-3-((2,2,2-trifluoroacetamido)methyl)benzoic acidYield 56,519.699%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2,6-dimethyl benzoic acid (6.8 g, 0.045 mmol) in conc. H2SO4 (100 mL), 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (7.1 g, 0.049 mmol) was added and the reaction mixture was stirred at RT for 24 h. After completion of the reaction, the reaction mass was quenched in ice water and stirred for 15 minutes. The obtained solid product was filtered and dried to afford 7.0 g of the desired title product. 1H NMR (300 MHz, DMSO d6): δ 2.26 (s, 6H), 4.36 (t, J=12.3 Hz, 2H), 7.09 (m, 1H), 7.15 (m, 1H), 9.89-9.94 (m, 1H).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mass was quenched in ice water
  3. stirringstirred for 15 minutes
  4. filtrationThe obtained solid product was filtered
  5. customdried

Sources & evidence

ORD record
ord-c521480019fd45eb94312a773d2c8503
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

Loading…