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

HRID 1469715

Reaction equation

HRID 1469715 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].OS(O)(=O)=O.[F:17][C:18]([F:25])([F:24])[C:19]([NH:21][CH2:22]O)=[O:20]>>[CH3:1][C:2]1[C:10]([CH2:22][NH:21][C:19](=[O:20])[C:18]([F:25])([F:24])[F:17])=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 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 87.2%

Procedure

To a solution of 2,6-dimethyl benzoic acid (2.0 g, 13.33 mmol) in cone. H2SO4 (4 mL) was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (2.1 g, 13.33 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was poured into ice-water and stirred for 2 h. The precipitate was collected by filtration and dried to afford 3.2 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 9.92 (m, 2H), 7.15-7.04 (m, 2H), 4.36 (s, 2H), 2.18 (m, 6H).

Workup

  1. stirringstirred for 2 h
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-bccdb023c533481da15a1d1c77024955
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Linked notes

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