Sodium → Methyl 2,3,5-trifluoro-6-methoxy-4-methylbenzoate

HRID 1722029Notes

Reaction equation

HRID 1722029 reaction equation
[CH3:1][C:2]1[C:11]([F:12])=[C:10](F)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:14])[C:3]=1[F:15].[CH3:16][O-:17].[Na+].[Na]>CO>[CH3:16][O:17][C:10]1[C:11]([F:12])=[C:2]([CH3:1])[C:3]([F:15])=[C:4]([F:14])[C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 14520264Methyl 2,3,5,6-tetrafluoro-4-methylbenzoate

Product 1

HCID 14520265Methyl 2,3,5-trifluoro-6-methoxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-methyl-2,3,5,6-tetrafluorobenzoate (1.0 g) was added to a solution of sodium methoxide obtained by dissolving sodium metal (0.15 g) in dry methanol (15 cm3) and the mixture heated at the reflux temperature for 2 hours until the reaction was complete. The product was purified by h.p.l.c. (Gilson) using a silica column and as eluent a mixture of petroleum ether (boiling range 40°-60° C., 1800 cm3) and diethyl ether (200 cm3), to obtain methyl 2-methoxy-4-methyl-3,5,6-trifluorobenzoate (0.38 g).

Workup

  1. customobtained
  2. temperaturethe mixture heated at the reflux temperature for 2 hours until the reaction
  3. customThe product was purified by h.p.l.c
  4. additionas eluent a mixture of petroleum ether (boiling range 40°-60° C., 1800 cm3) and diethyl ether (200 cm3)

Sources & evidence

ORD record
ord-7cd2332ad6e24096b94f91399150cbe4
Source dataset
uspto-grants-1989_08
Patent number
US04853414

Reaction notes

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