Malonic Acid → 5-[3-(4,4-Dimethoxycyclohex-1-en-1-yl)propyl]oxolan-2-one

HRID 596152Notes

Reaction equation

HRID 596152 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]2[O:15][C:14](=[O:16])[CH2:13][CH2:12]2)=[CH:4][CH2:3]1.C(O)(=O)C[C:19](O)=[O:20].[C:24](=O)(O)[O-].[Na+]>CO>[CH3:24][O:1][C:2]1([O:20][CH3:19])[CH2:7][CH2:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]2[O:15][C:14](=[O:16])[CH2:13][CH2:12]2)=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 516892Sodium BicarbonateHCID 214507515-[3-(4-Oxocyclohex-1-en-1-yl)propyl]oxolan-2-one

Product 1

HCID 214507545-[3-(4,4-Dimethoxycyclohex-1-en-1-yl)propyl]oxolan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 41 parts of tetrahydro-5-[3-(4-oxo-1-cyclohexen-1-yl)propyl]furan-2-one in 320 parts of methanol is added a solution of 20 parts of malonic acid in 160 parts of methanol. The resultant mixture is stirred at room temperatures for 7 hours, then cooled to 0°-5° and maintained thereat while being made basic with aqueous 5% sodium bicarbonate. The mixture thus obtained is extracted with ether. The ether extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is taken up in a 50:50 (by volume) mixture of ethyl acetate and hexane, and the resultant solution is filtered through silica gel. Solvent is removed from the filtrate by vacuum distillation, affording tetrahydro-5-[3-(4,4-dimethoxy-1-cyclohexen-1-yl)propyl]furan-2-one as the residue, an oil. It has the formula ##STR9##

Workup

  1. temperaturecooled to 0°-5°
  2. temperaturemaintained
  3. customThe mixture thus obtained
  4. extractionis extracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationstripped of solvent by vacuum distillation
  9. additionThe residue is taken up in a 50:50 (by volume) mixture of ethyl acetate and hexane
  10. filtrationthe resultant solution is filtered through silica gel
  11. customSolvent is removed from the filtrate by vacuum distillation

Sources & evidence

ORD record
ord-32edc96842214241bddc6b82547ddde0
Source dataset
uspto-grants-1977_03
Patent number
US04010169

Reaction notes

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