Methanol → HCID 19068287, compound

HRID 1957682Notes

Reaction equation

HRID 1957682 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([S:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(=O)(=O)(O)O.[CH3:35]O>>[C:1]12([C:11]3[CH:12]=[C:13]([S:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([O:27][CH3:35])=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 9953295HCID 9953295, compound

Product 1

HCID 19068287HCID 19068287, compound

Procedure

5 g (12.3 mmol) of 4-[3-(1-adamantyl)-4-methoxyphenylthiomethyl]benzoic acid and 50 ml of methanol were introduced into a round-bottomed flask and 330 μl of concentrated sulfuric acid were added. The mixture was heated at reflux for eight hours and the reaction medium was then evaporated to dryness. The residue was taken up in water, neutralized with sodium bicarbonate and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and hexane (40/60). After evaporation of the solvents, 4.1 g (79%) of methyl 4-[3-(1-adamantyl)-4-methoxyphenylthiomethyl]benzoate were recovered.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for eight hours
  3. customthe reaction medium was then evaporated to dryness
  4. extractionextracted with ethyl ether
  5. customThe organic phase was separated out
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customwas purified by chromatography on a column of silica
  10. washeluted with a mixture of dichloromethane and hexane (40/60)
  11. customAfter evaporation of the solvents, 4.1 g (79%) of methyl 4-[3-(1-adamantyl)-4-methoxyphenylthiomethyl]benzoate
  12. customwere recovered

Sources & evidence

ORD record
ord-f5ca1f62f88c4cc1b38e63ccbb7944bb
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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