2-Hydroxy-3-(2-methylphenyl)benzaldehyde → 2-Formyl-6-phenylphenol

HRID 25314Notes

Reaction equation

HRID 25314 reaction equation
[OH:1][C:2]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2C)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl.Cl.NC1C2C(=CC=CC=2O)C(S(O)(=O)=O)=CC=1N.S(=O)(O)[O-].[Na+]>CCO.O>[OH:1][C:2]1[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 110311532-Hydroxy-3-(2-methylphenyl)benzaldehydeHCID 23665763Sodium BisulfiteHCID 865878481,2-Diamino-8-hydroxy-naphthalene-4-sulfonic acid dihydrochloride

Product 1

HCID 107031002-Formyl-6-phenylphenolYield 155%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To an agitated solution of 2-hydroxy-3-(2′-methylphenyl)benzaldehyde (0.030 g, 0.14 mmol) in EtOH (0.80 mL) was added 1,2-diamino-8-hydroxy-naphthalene-4-sulfonic acid dihydrochloride (0.033 g, 0.10 mmol) and sodium bisulfite (0.03 g) in water (0.20 mL). The solution was heated to 60° C. and agitated over 18 hours. The solution was cooled to room temperature, the tan precipitate was isolated by filtration and washed with water and ethyl acetate to provide the title compound (0.043 g, 89%) MS(ES) m/z 445 [M−H].

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe tan precipitate was isolated by filtration
  3. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-b91e9af2cabb40b0934c87628c603c73
Source dataset
uspto-grants-2005_02
Patent number
US06858630B2

Reaction notes

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