Methanol → Bis(4-hydroxy-3,5-dimethylphenyl)methanone

HRID 2288253Notes

Reaction equation

HRID 2288253 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([CH3:18])[CH:11]=2)=[CH:4][C:3]=1[CH3:19].C[OH:21]>>[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([CH3:18])[CH:11]=2)=[O:21])=[CH:4][C:3]=1[CH3:19]

Participants

3

Reactant 2

HCID 887MethanolHCID 79345Bis(3,5-dimethyl-4-hydroxyphenyl)methane

Product 1

HCID 13742915Bis(4-hydroxy-3,5-dimethylphenyl)methanone

Procedure

To 20 ml methanol was dissolved 500 mg/2.0 mmol of bis(4-hydroxy-3,5-dimethylphenyl)methane, and 886 mg/4.0 mmol of dicyanodichloroquinone was added to the solution at once in a stream of argon. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the insoluble matter was separated by filtration and re-concentrated. The resulting crude product was purified by silica gel column chromatography using methylene chloride for the eluting solution to obtain 230 mg of the desired 4,4'-dihydroxy-3,3',5,5'-tetramethylbenzophenone. MS: 270 (M+), 1H-NMR (CDCl3 /DMSO-d6): δ2.29 (12H, s), 7.41 (4H, s), 7.96 (2H, s).

Workup

  1. additionwas added to the solution at once in a stream of argon
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe insoluble matter was separated by filtration
  5. concentrationre-concentrated
  6. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfc208e7948e4cffa519f36d944fff48
Source dataset
uspto-grants-2000_07
Patent number
US06087502

Reaction notes

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