Methyl Salicylate → HCID 21435326, compound

HRID 268357Notes

Reaction equation

HRID 268357 reaction equation
[C:1]([O:10]C)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:12]([N:14]([CH2:19][CH3:20])[CH2:15][CH2:16]CCl)[CH3:13].[C:21](=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:19]([N:14]([CH2:12][CH3:13])[CH:15]([CH3:16])[CH2:21][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])[CH3:20]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 669183-Chloropropyl(diethyl)amine

Product 1

HCID 21435326HCID 21435326, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 15.2 g. (0.10 mol.) of methyl salicylate, 16.45 g. (0.11 mol.) of 3-diethylaminopropyl chloride and 27.7 g. (0.20 mol.) of potassium carbonate in 250 ml. of 2-butanone is refluxed for 22 hours to give 2-(2-diethylaminopropoxy)benzoic acid which is converted to the corresponding hydrochloride salt by heating with 100 ml. of concentrated hydrochloric acid for three hours, m.p. 137°-140°.

Workup

  1. additionA mixture of 15.2 g

Sources & evidence

ORD record
ord-37f487d1c20742bd966c91b2a1cf3ac4
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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