Ethyl Salicylate → HCID 19905970, compound

HRID 2371665Notes

Reaction equation

HRID 2371665 reaction equation
CN(C)C(=O)C.[C:7]([O:16]CC)(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].C(=O)([O-])[O-].[K+].[K+].S(O[CH2:30][CH:31]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=O)(=O)C>C(OCC)(=O)C.O>[CH2:40]([CH:31]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:30][O:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[C:7]([OH:16])=[O:15])[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 4

HCID 8365Ethyl SalicylateHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 14596246111360-16-8

Product 1

HCID 19905970HCID 19905970, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

300 ml of N,N-dimethylacetamide was added to 17.5 g of ethyl salicylate, and 34.6 g of potassium carbonate and then 32.1 of 2-hexyldecyl mesylate were added dropwise over about 30 min with stirring on a steam bath. After the addition the stirring was continued for 2 hours further under heating, and then the reaction mixture was cooled and transferred into a separately funnel. Then 300 ml of ethyl acetate and 1l of water were added for extraction. The ethyl acetate solution was washed with dilute hydrochloric acid, and then with an aqueous sodium hydrogencarbonate solution, and it was concentrated. 300 ml of ethanol was to the coil concentrate, to dissolve the concentrate, and a solution, of 12 g of sodium hydroxide in 50 ml of water was added dropwise thereto over about 10 min at room temperature with stirring. After the addition the stirring was continued for 1 hour further and 30 ml of concentrated hydrochloric acid diluted with 300 ml of water was added dropwise. The reaction liquid was transferred into a separately funnel, and 500 ml of water and 300 ml of ethyl acetate were added for extraction. The ethyl acetate solution was washed with 500 ml of water twice and then concentrated, to obtain 36.0 g of 2-(2-hexyldecyloxy)benzoic acid in the form of an oil.

Workup

  1. additionAfter the addition the stirring
  2. temperaturefurther under heating
  3. temperaturethe reaction mixture was cooled
  4. washThe ethyl acetate solution was washed with dilute hydrochloric acid
  5. concentrationwith an aqueous sodium hydrogencarbonate solution, and it was concentrated
  6. concentrationconcentrate
  7. dissolutionto dissolve the concentrate
  8. additiona solution, of 12 g of sodium hydroxide in 50 ml of water was added dropwise
  9. stirringover about 10 min at room temperature with stirring
  10. additionAfter the addition the stirring
  11. waitwas continued for 1 hour
  12. additionfurther and 30 ml of concentrated hydrochloric acid diluted with 300 ml of water
  13. additionwas added dropwise
  14. customThe reaction liquid
  15. additionwere added for extraction
  16. washThe ethyl acetate solution was washed with 500 ml of water twice
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-fe424e2ae65a49228bbcadff8f683509
Source dataset
uspto-grants-1992_03
Patent number
US05094938

Reaction notes

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