p-Toluenesulfonic acid monohydrate → HCID 54069142, compound

HRID 1647994Notes

Reaction equation

HRID 1647994 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]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21]C(=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][C:7]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]

Participants

4

Reactant 2

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

Product 1

HCID 54069142HCID 54069142, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.22 g (12.06 mmol) of 2-[[5-(acetyloxy)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-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-3e46a37068d54fed9a7828674f593ef9
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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