p-Toluenesulfonic acid monohydrate → HCID 53928679, compound

HRID 327964Notes

Reaction equation

HRID 327964 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19]C)=[O:17])[CH:9]=[CH:8][C:7]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27]C1CCCCO1.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[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:9]=[CH:8][C:7]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 54461391HCID 54461391, compound

Product 1

HCID 53928679HCID 53928679, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.26 g (8.91 mmol) of rac-2-[6-[(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy]hexyl]-5-(4-ethoxy-4-oxobutoxy)benzenepropanoic acid methyl ester, 0.16 g of p-toluenesulfonic acid monohydrate, and 75 mL of methanol was stirred and refluxed for 24 hr. 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 flash-chromatographed on silica gel, eluting with 1:1 hexane-ethyl acetate. There was obtained 2.0 g (59%) of 2-(6-hydroxyhexyl)-5-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester as a colorless oil.

Workup

  1. temperaturerefluxed for 24 hr
  2. customThe 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 flash-chromatographed on silica gel
  7. washeluting with 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-07771c3c8d5b4a82a1e38530dbfe1c6a
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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