Potassium Dichromate → HCID 11323174, compound

HRID 1099425Notes

Reaction equation

HRID 1099425 reaction equation
[F:1][C:2]([F:16])([F:15])[S:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:18].[K+].[K+]>S(=O)(=O)(O)O>[F:16][C:2]([F:15])([F:1])[S:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]([OH:18])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 24502Potassium DichromateHCID 108796304-(trifluoromethanesulfonyloxy)benzaldehyde

Product 1

HCID 11323174HCID 11323174, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 4-(trifluoromethanesulfonyloxy)benzaldehyde (5.2 g, 20.5 mmol, described in JACS, 1987, 109, 5478) and potassium dichromate (2.5 g) in sulfuric acid (30%, 47 mL) was heated at 65° C. for 1 h. The mixture was allowed to cool to ambient temperature and then poured on ice. The formed precipitate was filtered off and washed with several portions of water. The crude product was recrystallized from water/ethanol (1:1) affording 2.63 g (47% yield) of the title compound: mp 178-180° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.11 (d, 2 H), 7.64 (d, 2 H).

Workup

  1. temperatureto cool to ambient temperature
  2. additionpoured on ice
  3. filtrationThe formed precipitate was filtered off
  4. washwashed with several portions of water
  5. customThe crude product was recrystallized from water/ethanol (1:1)

Sources & evidence

ORD record
ord-bb38fb584f234dfe959df0e7025f3b6c
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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