4-Mercaptobenzoic acid → 4-[3-(1-Adamantyl)-4-methoxyethoxymethoxybenzoylthio]benzoic acid

HRID 1957707Notes

Reaction equation

HRID 1957707 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]12([C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[C:24](Cl)=[O:25])[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2>N1C=CC=CC=1>[C:11]12([C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[C:24]([S:1][C:2]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=3)=[O:25])[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:19]3)[CH2:18]1)[CH2:20]2

Participants

4

Reactant 2

HCID 957384-Mercaptobenzoic acidHCID 572331023-(1-Adamantyl)-4-methoxyethoxymethoxybenzoyl chloride

Product 1

HCID 882978354-[3-(1-Adamantyl)-4-methoxyethoxymethoxybenzoylthio]benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.54 g (10 mmol) of 4-mercaptobenzoic acid and 40 ml of pyridine were introduced into a round-bottomed flask. A solution of 3.75 g (10 mmol) of 3-(1-adamantyl)-4-methoxyethoxymethoxybenzoyl chloride prepared in Example 10(c) was added dropwise and the mixture was stirred at room temperature for six hours. The mixture was evaporated to dryness, the residue was taken up in water and ethyl ether. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The solid obtained was recrystallized from a diisopropyl ether/methanol mixture, filtered off and dried. 2.94 g (59%) of 4-[3-(1-adamantyl)-4-methoxyethoxymethoxybenzoylthio]benzoic acid, having a melting point of 187°-8° C., were recovered.

Workup

  1. customThe mixture was evaporated to dryness
  2. customThe organic phase was separated out
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe solid obtained
  7. customwas recrystallized from a diisopropyl ether/methanol mixture
  8. filtrationfiltered off
  9. customdried
  10. customwere recovered

Sources & evidence

ORD record
ord-0b3c9a405116418498dfa8313a777ceb
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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