Hexamethylenetetramine → 4-Hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 2112853Notes

Reaction equation

HRID 2112853 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[OH:9][C:4]1[CH:5]=[CH:6][C:7]([CH:24]=[O:25])=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 679582-Trifluoromethylphenol

Product 1

HCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehydeYield 36%

Procedure

A solution of 2-trifluoromethyl phenol (5.0 g, 30.86 mmol) and hexamethylenetetramine (8.64 g, 61.72 mmol) in trifluoracetic acid (50 mL) was heated at 65° C. for 18 h. At the end of this time the solution was concentrated and diluted with a 2N aqueious solution of hydrochloric acid. The acid phase was extracted twice with ethyl acetate and the combined organic extract dried over magnesium sulfate and concentrated. The residue was subjected to chromatography via Biotage (FLASH 40 M, silica, 20% ethyl acetate/hexane) to yield 2.1 g (36%) of 4-hydroxy-3-(trifluoromethyl)benzaldehyde. MS (ES) m/z 188.9; HRMS: calcd for C8H5F3O2, 190.0242; found (ESI, [M+H]+), 191.0324.

Workup

  1. concentrationAt the end of this time the solution was concentrated
  2. additiondiluted with a 2N aqueious solution of hydrochloric acid
  3. extractionThe acid phase was extracted twice with ethyl acetate
  4. extractionthe combined organic extract
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5de962b406904033a393786b02347b59
Source dataset
uspto-grants-2009_04
Patent number
US07524846B2

Reaction notes

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