p-Toluenesulfonic acid monohydrate → HCID 85720616, compound

HRID 327954Notes

Reaction equation

HRID 327954 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][C:7]=1OCCCCCOC(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53767267HCID 53767267, compound

Product 1

HCID 85720616HCID 85720616, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.22 g (12.06 mmol) of 2-[[5-(acetoxy)pentyl]oxy]-5-acetylbenzenepropanoic acid methyl ester and 0.1 g of p-toluenesulfonic acid monohydrate in 50 mL of methanol was stirred and refluxed for 3.5 hr and stirred at room temperature for 21 hr. Most of the methanol was removed in vacuo and the residue was diluted with water and worked-up with ether in the usual manner (the combined ether extracts were additionally washed with saturated aqueous sodium bicarbonate). The product was purified by flash chromatography on silica gel, eluting with 1:2 hexane-ethyl acetate. There was obtained 3.6 g (97%) of 2-[[5-(acetoxy)pentyl]oxy]phenyl]-2-propenoic hydroxypentyl)oxy]-5-acetylbenzenepropanoic acid methyl ester as a viscous oil.

Workup

  1. temperaturerefluxed for 3.5 hr
  2. customMost of the methanol was removed in vacuo
  3. additionthe residue was diluted with water
  4. washwere additionally washed with saturated aqueous sodium bicarbonate)
  5. customThe product was purified by flash chromatography on silica gel
  6. washeluting with 1:2 hexane-ethyl acetate

Sources & evidence

ORD record
ord-9f96f6be0fcb4fb18bbf6a0a48a64b95
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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