Methyl Salicylate → HCID 14739009, compound

HRID 358825Notes

Reaction equation

HRID 358825 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl[CH2:13][C:14]([CH3:16])=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][C:14](=[CH2:13])[CH2:16][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 14739009HCID 14739009, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 152 g of methyl salicylate, 99 g of 3-chloro-2-methylpropene, 151.8 g of potassium carbonate, and 500 ml of acetone was heated at reflux overnight. After cooling, the mixture was extracted with diethyl ether and ethyl acetate. The organic extracts were combined, washed twice with a 10% sodium chloride solution and water, dried over sodium sulfate, and concentrated in vacuo. The resulting liquid was vacuumed distilled. The fraction collected at 120°-121° C. and 1.5 torr provided 76.2 g of the desired subtitle intermediate. NMR, MS.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with diethyl ether and ethyl acetate
  5. washwashed twice with a 10% sodium chloride solution and water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationThe resulting liquid was vacuumed distilled
  9. customThe fraction collected at 120°-121° C.

Sources & evidence

ORD record
ord-81edd37476fd4553ba048c6630da3eda
Source dataset
uspto-grants-1991_03
Patent number
US04997956

Reaction notes

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