Hydrochloric Acid → 5-tert-Butyl-2-hydroxy-3-(methanesulfonyl)benzaldehyde

HRID 543370Notes

Reaction equation

HRID 543370 reaction equation
Cl.N[CH2:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([S:14]([CH3:17])(=[O:16])=[O:15])[C:5]=1[OH:18].C1N2CN3CN(C2)CN1C3.Cl.FC(F)(F)C(O)=[O:33]>>[CH:3]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([S:14]([CH3:17])(=[O:16])=[O:15])[C:5]=1[OH:18])=[O:33]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 10402160HCID 10402160, compound

Product 1

HCID 134237195-tert-Butyl-2-hydroxy-3-(methanesulfonyl)benzaldehyde

Procedure

14.65 g (0.05 mol) of 2-aminomethyl-4-(1,1-dimethylethyl)-6-methylsulfonylphenol hydrochloride are dissolved in 100 ml of trifluoroacetic acid, 9 g (0.065 mol) of urotropine (hexamethylenetetraamine) are added, and the mixture is boiled under reflux for 2.5 h. Then 50 ml of 4 N hydrochloric acid are added, the mixture is again boiled under reflux for 10 minutes, and the reaction mixture is poured onto ice-water and filtered with suction. Pale yellow crystals of melting point: 134°-136° C.

Workup

  1. temperatureunder reflux for 2.5 h
  2. temperatureunder reflux for 10 minutes
  3. additionthe reaction mixture is poured onto ice-water
  4. filtrationfiltered with suction

Sources & evidence

ORD record
ord-fc70462efd6c45659e9169b8717b2d49
Source dataset
uspto-grants-1987_04
Patent number
US04661636

Reaction notes

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