Hexamethylenetetramine → 2-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde

HRID 1710000Notes

Reaction equation

HRID 1710000 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:25](O)=[O:26]>O>[OH:12][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:6][C:5]=1[CH:25]=[O:26]

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 134994724-tert-Butyl-3-chlorophenol

Product 1

HCID 230354272-Hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehydeYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.65 g (52.2 mmol) of 3-chloro-4-(1,1-dimethylethyl)phenol and 7.37 g (52.2 mmol) of hexamethylenetetramine was refluxed in 150 ml of trifluoroacetic acid for 3 hours. The solution was cooled to ambient temperature and diluted with 500 ml of water. The aqueous residue was extracted with ether. The organic phase was washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was chromatographed on 250 g of silica gel using a gradient from hexane to 20:80 (v/v) ether: hexane as eluent. There was obtained 1.87 g (8.79 mmol, 17%) of 2-hydroxy-4-chloro-5-(1,1-dimethylethyl)benzaldehyde; mp 38°-39° C.

Workup

  1. extractionThe aqueous residue was extracted with ether
  2. washThe organic phase was washed with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed on 250 g of silica gel using a gradient from hexane to 20:80 (v/v) ether

Sources & evidence

ORD record
ord-375129a6d5c34d1b9ba00aca701d145e
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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