Methyl 11-(4-methylphenylsulfonyloxy)undecanoate → Undecanoic acid, 11-oxo-, methyl ester

HRID 1709639Notes

Reaction equation

HRID 1709639 reaction equation
CC1C=CC(S([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])(=O)=O)=CC=1>CS(C)=O>[O:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]

Participants

3

Reactant 1

HCID 14855872Methyl 11-(4-methylphenylsulfonyloxy)undecanoate

Product 1

HCID 11020258Undecanoic acid, 11-oxo-, methyl esterYield 98.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dimethylsulfoxide, 178 ml, was heated to 150° C. as nitrogen was bubbled through it. Sodium bicarbonate, 23.7 grams (0.282 mole), was added portionwise while maintaining the reaction mixture temperature at 140°-160° C. Upon completion of addition, 13.6 grams (0.037 mole) of methyl 11-(4-methylphenylsulfonyloxy)undecanoate was added portionwise during a ten minute period. Upon completion of addition the reaction mixture was allowed to cool to ambient temperature, and then it was poured into 600 ml of ice-water. The mixture was stirred until the ice melted, and then it was extracted with three portions of heptane. The combined extracts were washed with three portions of water followed by two portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 7.8 grams of methyl 11-oxoundecanoate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customwas bubbled through it
  2. additionSodium bicarbonate, 23.7 grams (0.282 mole), was added portionwise
  3. temperaturewhile maintaining the reaction mixture temperature at 140°-160° C
  4. additionwas added portionwise during a ten minute period
  5. additionUpon completion of addition the reaction mixture
  6. extractionit was extracted with three portions of heptane
  7. washThe combined extracts were washed with three portions of water
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-37ad605c9f3141629b4e09b97b7bafb0
Source dataset
uspto-grants-1990_08
Patent number
US04950666

Reaction notes

Loading…