Hydrochloric Acid → 4-Methoxy-3,5,6-trifluorophthalic acid-1-methyl ester

HRID 259959Notes

Reaction equation

HRID 259959 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[C:9]([F:16])[C:10](F)=[C:11]([F:14])[C:12]=1[F:13])[C:6]([OH:8])=[O:7].[CH3:18][O-:19].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[C:9]([F:16])[C:10]([O:19][CH3:18])=[C:11]([F:14])[C:12]=1[F:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108579443,4,5,6-Tetrafluorophthalic acid-monomethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 109452904-Methoxy-3,5,6-trifluorophthalic acid-1-methyl esterYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a 100 ml glass reactor equipped with a reflux condenser, a stirrer and a dropping funnel, 20 ml of a methanol solution of 10 g (0.0397 mol) of the 3,4,5,6-tetrafluorophthalic acid-monomethyl ester prepared in Example 14, was charged. Then, 44.9 g (0.0833 mol) of a 10% methanol solution of sodium methoxide was dropwise added thereto. The mixture was stirred for one hour under reflux. After completion of the reaction, the reaction mixture was neutralized with a 10% hydrochloric acid aqueous solution and extracted with ethyl acetate. Then, the solvent was distilled off to obtain 9.14 g of 4-methoxy-3,5,6-trifluorophthalic acid-1-methyl ester. (=5-methoxy-3,4,6-trifluorophthalic acid-2-methyl ester.) The yield was 87.2%.

Workup

  1. customInto a 100 ml glass reactor equipped with a reflux condenser, a stirrer and a dropping funnel
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-75fe526cfff2450ba5fb78201217459b
Source dataset
uspto-grants-1996_06
Patent number
US05523476

Reaction notes

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