Methyl Salicylate → HCID 12361482, compound

HRID 1728803Notes

Reaction equation

HRID 1728803 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CC(C)=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 8208Myristyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 12361482HCID 12361482, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 40 g of methyl 2-hydroxybenzoate, 45.4 g of powdered potassium carbonate, 700 ml acetone and 78.2 g of 1-bromotetradecane is heated at reflux temperature for 5 days. The reaction is cooled, filtered and concentrated in vacuo. The residue is dissolved in ethyl acetate; washed with water, saturated sodium bicarbonate, 10% sodium hydroxide, water and saturated sodium chloride; dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane) to give 46.0 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 5 days
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed with water, saturated sodium bicarbonate, 10% sodium hydroxide, water and saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3f278d9c059d4ccd8a32d22df8b40a74
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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