p-Toluenesulfonic acid monohydrate → HCID 54501316, compound

HRID 327961Notes

Reaction equation

HRID 327961 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:10]=[CH:9][C:8]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]C(=O)C)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:10]=[CH:9][C:8]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 54171091HCID 54171091, compound

Product 1

HCID 54501316HCID 54501316, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.0 g (2.2 mmol) of 2-[[5-(acetyloxy)pentyl]oxy]-5-(4-ethoxy-4-oxobutoxy)benzenepropanoic acid ethyl ester from the preceding example, and 0.018 g of p-toluenesulfonic acid monohydrate in 10 mL of ethanol was stirred and refluxed for 30 hr and stirred at room temperature for 21 hr. Most of the ethanol 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 1:1 hexane-ethyl acetate. There was obtained 0.6 g (66.5%) of 2-[(5-hydroxypentyl)oxy]-5-(4-ethoxy-4-oxobutoxy)benzenepropanoic acid ethyl ester as a viscous oil.

Workup

  1. temperaturerefluxed for 30 hr
  2. customMost of the ethanol 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 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-3ab12845fdd7487ebe72e9240650da0d
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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