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

HRID 508846Notes

Reaction equation

HRID 508846 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-8129dc9bf9414d85ab2fde8fefb8eff5
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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