Methanol → HCID 14430179, compound

HRID 1731650Notes

Reaction equation

HRID 1731650 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH2:3]1.[CH3:13]O>S(=O)(=O)(O)O>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 202283473-(4-Oxocyclohex-1-en-1-yl)propanoic acid

Product 1

HCID 14430179HCID 14430179, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3.5 g of 4-oxocyclohex-1-enepropionic acid in 16.5 ml of methanol and 0.9 ml of concentrated sulfuric acid was refluxed for 30 minutes. The mixture was cooled and the solvent was evaporated under reduced pressure. The resulting residue was partitioned between 50 ml of 5% aqueous sodium bicarbonate and 100 ml of ether. The separated aqueous layer was washed twice with 100-ml portions of ether and the washings were combined with the original organic layer and dried over magnesium sulfate. The solvent was evaporated to give a crude product which was found to be a 1:1 mixture of double bond isomers by NMR analysis. Flash chromatography of this crude product (silica gel, 3:7 ethyl acetate-hexane) separated the compounds and gave methyl 4-oxocyclohex-2-enepropionate as a clear oil. 1H NMR (CDCl3) δ 3.60 (s, 3H); 5.70-6.00 (dd, 1H); 6.60-6.95 (d of m, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was partitioned between 50 ml of 5% aqueous sodium bicarbonate and 100 ml of ether
  4. washThe separated aqueous layer was washed twice with 100-ml portions of ether
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a crude product which
  8. additiona 1:1 mixture of double bond isomers by NMR analysis
  9. customFlash chromatography of this crude product (silica gel, 3:7 ethyl acetate-hexane) separated the compounds

Sources & evidence

ORD record
ord-34fc586212934e0aae4dae348d8443d5
Source dataset
uspto-grants-1986_11
Patent number
US04622422

Reaction notes

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