Salicylic Acid → 2-Acetyloxybenzoic acid 6-(chloromethyl)-2methylpyridinyl ester

HRID 1166193Notes

Reaction equation

HRID 1166193 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][Cl:20])[N:14]=1.[CH2:21]([O:23]CC)[CH3:22]>CN(C=O)C>[Cl:20][CH2:19][C:15]1[N:14]=[C:13]([CH3:12])[C:18]([O:9][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4][C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 3283Diethyl EtherHCID 3166542,6-Bis(chloromethyl)pyridine

Product 1

HCID 688807642-Acetyloxybenzoic acid 6-(chloromethyl)-2methylpyridinyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of salicylic acid (1.6 g, 8.88 mmoles) in N,N′-dimethylformamide (20 ml) and under stirring sodium ethylate (0.64 g, 8.88 mmoles) is added. After 30 minutes the obtained solution is added to a solution of 2,6-bis-(chloromethyl)pyridine (4.72 g, 26.81 mmoles) in N,N′-dimethylformamide (20 ml). The solution is left at room temperature for 7 days, under stirring, then is diluted with ethyl ether and washed with water. The separated organic phases are anhydrified with sodium sulphate and the solvent is evaporated at reduced pressure. The reaction crude product is purified by chromatography on silica gel by eluting with n-hexane/ethyl acetate 7/3. 1.7 g of the product as yellow oil are obtained.

Workup

  1. washwashed with water
  2. customthe solvent is evaporated at reduced pressure
  3. customThe reaction crude product
  4. customis purified by chromatography on silica gel
  5. washby eluting with n-hexane/ethyl acetate 7/3

Sources & evidence

ORD record
ord-b05a90314d204242a2ac14f8fc776bbd
Source dataset
uspto-grants-2003_09
Patent number
US06613784B1

Reaction notes

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