Sodium methanethiolate → (4-tert-Butylphenyl)(4-hydroxyphenyl)methanone

HRID 1857120Notes

Reaction equation

HRID 1857120 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.C[S-].[Na+]>CN(C)C=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 101992554-t-Butylphenyl 4-methoxyphenyl ketone

Product 1

HCID 108659(4-tert-Butylphenyl)(4-hydroxyphenyl)methanoneYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-t-Butylphenyl 4-methoxyphenyl ketone (862 mg) obtained in Example 29 was dissolved in N,N-dimethylformamide (35 ml), sodium thiomethoxide (562 mg) was added, and the admixture was refluxed for 3 hours under argon. The reaction mixture was partitioned between 10% aqueous phosphoric acid and ethyl acetate. The ethyl acetate layer was then dried with anhydrous magnesium sulfate and the solvent was removed by reduced-pressure distillation to obtain 794 mg of the title compound (yield: 97%).

Workup

  1. temperaturethe admixture was refluxed for 3 hours under argon
  2. customThe reaction mixture was partitioned between 10% aqueous phosphoric acid and ethyl acetate
  3. dry with materialThe ethyl acetate layer was then dried with anhydrous magnesium sulfate
  4. customthe solvent was removed by reduced-pressure distillation

Sources & evidence

ORD record
ord-5526a4b58b784bfda7bf6e06fa878883
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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