Pyridine → 4-[3-Tert.butyl-4-methoxybenzoylthio]benzoic acid

HRID 1681572Notes

Reaction equation

HRID 1681572 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].[SH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.N1C=CC=CC=1>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([S:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 957384-Mercaptobenzoic acidHCID 10488578Benzoic acid, 3-(1,1-dimethylethyl)-4-methoxy-2×

Product 1

HCID 198051694-[3-Tert.butyl-4-methoxybenzoylthio]benzoic acidYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 3-(tert.butyl)-4-methoxybenzoic acid, prepared starting with 1.04 g (5 mmoles) of 3-(tert.butyl)-4-methoxybenzoic acid, described in Example 35 of French Patent No. 85 13747 (2.570.377), is dissolved in 15 ml of dichloromethane. The solution is slowly added to a mixture of 771 mg (5 mmoles) of 4-mercaptobenzoic acid and 8 ml of pyridine. The reaction mixture is stirred at ambient temperature for 8 hours, evaporated to dryness, taken up in water, acidified to pH 5 with 1N HCl and extracted with ethyl ether. The organic phase is decanted, washed with water, dried over magnesium sulfate and evaporated to dryness. The resulting residue is purified by chromatography on a silica column (eluant: ethyl ether). The solvent is evaporated and 530 mg (32% yield) of 4-[3-tert.butyl-4-methoxybenzoylthio]benzoic acid whose melting point is 220°-221° C. are obtained.

Workup

  1. customevaporated to dryness
  2. extractionextracted with ethyl ether
  3. customThe organic phase is decanted
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe resulting residue is purified by chromatography on a silica column (eluant: ethyl ether)
  8. customThe solvent is evaporated

Sources & evidence

ORD record
ord-4ca641af673646629be97e70c6a50fcf
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

Loading…