Benzaldehyde, 2,4,6-trihydroxy- → HCID 178449927, compound

HRID 1740928Notes

Reaction equation

HRID 1740928 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=O.[C:12]([NH:16][OH:17])([CH3:15])([CH3:14])[CH3:13]>C1C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[N+:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[O-:17]

Participants

6

Reactant 2

HCID 68099Benzaldehyde, 2,4,6-trihydroxy-HCID 98586N-tert-butylhydroxylamine

Product 1

HCID 178449927HCID 178449927, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4,6-Trihydroxybenzaldehyde (17.69 g, 0.115 mole) was added to a solution of N-tert-butyl hydroxylamine (14.32 g, 0.161 mole) in benzene (250 mL). p-Toluenesulfonic acid (15 mg) was added and the reaction vessel fitted with a Dean-Stark trap. The reaction was heated at reflux for 88 hours under nitrogen and then diluted with 500 mL of ethyl acetate. The solution was washed with water, brine and dried over sodium sulfate. The product was recrystallized from ethanol/water and then dried in vacuo for 2 hr at 35° C. to provide 16.95 g (65.5% yield) of the title compound. The product had a melting point of 189.9-190.3° C. and an Rf on silica gel TLC (50% hexane, 45% ethyl acetate, 5% methanol) of 0.31 (2,4,6-trihydroxybenzaldehyde Rf=0.47).

Workup

  1. customthe reaction vessel fitted with a Dean-Stark trap
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 88 hours under nitrogen
  4. washThe solution was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe product was recrystallized from ethanol/water
  7. customdried in vacuo for 2 hr at 35° C.

Sources & evidence

ORD record
ord-13f150bdce3649e09588791d07495ae0
Source dataset
uspto-grants-1999_10
Patent number
US05972977

Reaction notes

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