2-Formyl-5-(2-methylphenyl)phenol → 2-hydroxy-4-phenylbenzaldehyde

HRID 25315Notes

Reaction equation

HRID 25315 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2C)[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[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 225667242-Formyl-5-(2-methylphenyl)phenolHCID 23665763Sodium BisulfiteHCID 865878481,2-Diamino-8-hydroxy-naphthalene-4-sulfonic acid dihydrochloride

Product 1

HCID 115792992-hydroxy-4-phenylbenzaldehydeYield 104.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To an agitated solution of 2-hydroxy-4-(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 (0.029 g, 60%) 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-e1675aaf8d5e4b36997b0c8196f52094
Source dataset
uspto-grants-2005_02
Patent number
US06858630B2

Reaction notes

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