p-Toluenesulfonic acid monohydrate → 2-(6-Hydroxyhexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester

HRID 2210084Notes

Reaction equation

HRID 2210084 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]C2CCCCO2)=[CH:10][CH:9]=[CH:8][C:7]=1[O:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32]C)=[O:30].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[C:7]([O:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53666033rac-2-(4-Ethoxy-4-oxobutoxy)-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]benzenepropanoic acid methyl ester

Product 1

HCID 537776932-(6-Hydroxyhexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 9.74 g (ca. 20 mmol) of rac-2-(4-ethoxy-4-oxobutoxy)-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]benzenepropanoic acid methyl ester from the preceding example, and 0.53 g of p-toluenesulfonic acid monohydrate, in 270 mL of methanol was stirred and refluxed for 21.5 hr. Most of the solvent was removed in vacuo and the residue was dissolved in ether. The ether solution was washed with saturated sodium bicarbonate solution and processed in the usual manner giving an oil. This material was chromatographed on 200 g of silica gel, eluting with hexane-ethyl acetate mixtures. There was obtained 7.03 g (92.5%) of 2-(6-hydroxyhexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester as a colorless oil.

Workup

  1. temperaturerefluxed for 21.5 hr
  2. customMost of the solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ether
  4. washThe ether solution was washed with saturated sodium bicarbonate solution
  5. customgiving an oil
  6. customThis material was chromatographed on 200 g of silica gel
  7. washeluting with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-d82fc85666f34e59bae3ee9fd2e93cce
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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