Sodium methanethiolate → 4-n-Butylphenyl 4-hydroxyphenyl ketone

HRID 1857216Notes

Reaction equation

HRID 1857216 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]([CH2:17][CH2:18][CH2:19][CH3:20])=[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]([CH2:17][CH2:18][CH2:19][CH3:20])=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 12343545(4-Butylphenyl)(4-methoxyphenyl)methanone

Product 1

HCID 221326794-n-Butylphenyl 4-hydroxyphenyl ketoneYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-n-Butylphenyl 4-methoxyphenyl ketone (863 mg) obtained in Example 147 was dissolved in N,N-dimethylformamide (50 ml), sodium thiomethoxide (563 mg) was added, and the admixture was refluxed with heat for 7 hours under argon. The reaction mixture was treated in the same manner as described in Example 33 to obtain 787 mg of the title compound (yield: 96%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 7 hours under argon
  3. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-7ccfce32019f4a41b56cdceeadb6b3b9
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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