Diethyl Ether → Methyl 4-chloro-2-hydroxybenzoate

HRID 1279625Notes

Reaction equation

HRID 1279625 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[CH3:12]COCC>[N+](=C)=[N-]>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 2

HCID 3283Diethyl Ether2×HCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 9550DiazomethaneSolvent

Procedure

To a solution of 4-chloro-2-hydroxybenzoic acid (5.0 g) in ether (50 ml), diazomethane in ether was added until the reaction was terminated at 0° C. The reaction mixture was concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=4:1) to give the title compound (5.4 g) having the following physical data.

Workup

  1. customwas terminated at 0° C
  2. concentrationThe reaction mixture was concentrated under the reduced pressure
  3. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=4:1)

Sources & evidence

ORD record
ord-3c9fba86632b4aa9b72547800c740610
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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