Sulfuryl chloride → Methyl 5-chloro-4-carboxymethyl-2-methoxy-benzoate

HRID 222846Notes

Reaction equation

HRID 222846 reaction equation
[C:1]([CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1)([OH:3])=[O:2].S(Cl)([Cl:20])(=O)=O>C(O)(=O)C>[Cl:20][C:14]1[C:5]([CH2:4][C:1]([OH:3])=[O:2])=[CH:6][C:7]([O:15][CH3:16])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 108229932-(3-Methoxy-4-(methoxycarbonyl)phenyl)acetic acid

Product 1

HCID 68967398Methyl 5-chloro-4-carboxymethyl-2-methoxy-benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 300 mg of methyl 4-carboxymethyl-2-methoxy-benzoate from preparation 1 placed in 6 mL of acetic acid, are added 110 μL of sulfuryl chloride (1 equivalent). The whole is refluxed for 6 hours. After evaporation of the solvent, the reaction crude product is purified on silica gel (petroleum ether/ethyl acetate: 80/20 then 60/40) leading to 165 mg of the desired compound.

Workup

  1. temperatureThe whole is refluxed for 6 hours
  2. customAfter evaporation of the solvent
  3. customthe reaction crude product
  4. customis purified on silica gel (petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-06769f0d1185415495eb12682526afc1
Source dataset
uspto-grants-2012_06
Patent number
US08207373B2

Reaction notes

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