Sulfuric Acid → 3,5-difluoro-2-hydroxybenzaldehyde

HRID 2420641Notes

Reaction equation

HRID 2420641 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)O.FC(F)(F)[C:27](O)=[O:28]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH:27]=[O:28])[C:3]=1[OH:9]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 1230512,4-Difluorophenol

Product 1

HCID 27793743,5-difluoro-2-hydroxybenzaldehyde

Conditions

Temperature
75 °C

Procedure

260 g (2.00 mol) of 2,4-difluorophenol are dissolved in 1.6 l of trifluoroacetic acid, and 560 g (4.00 mol) of hexamethylenetetramine are added in portions. After 30 min, the batch is warmed to 75° C. and stirred overnight. 2 l of 40 percent sulfuric acid are subsequently added at RT, the mixture is left to stir for 2.5 h, 1.5 l of ice-water are added, and the mixture is stirred for a further 30 min. The deposited precipitate is separated off, washed with water and taken up in dichloromethane. The resultant solution is dried over sodium sulfate and evaporated, giving 3,5-difluorosalicylaldehyde as a beige solid.

Workup

  1. waitthe mixture is left
  2. stirringto stir for 2.5 h
  3. stirringthe mixture is stirred for a further 30 min
  4. customThe deposited precipitate is separated off
  5. washwashed with water
  6. dry with materialThe resultant solution is dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-634de28b653c4bbc870b8f367bccf9c6
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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