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

HRID 1650620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650620
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-08182d4b8b6741f0b29a271d06e46859
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925658

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