Tetramethyltin → Methyl 5-formyl-2-methylbenzoate

HRID 2221631Notes

Reaction equation

HRID 2221631 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6](OS(C(F)(F)F)(=O)=O)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].[CH3:21][Sn](C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 15466849Methyl 5-formyl-2-(trifluoromethylsulfonyloxy)benzoate

Product 1

HCID 19700886Methyl 5-formyl-2-methylbenzoateYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 5-formyl-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (4.88 g), tetramethyltin (10.8 g), tetrakis(triphenylphosphine)palladium (1.85 g) and toluene (150 mL) was heated under reflux for 20 hrs. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography to give methyl 5-formyl-2-methylbenzoate as colorless crystals (2.31 g, yield 83%) from a fraction eluted with ethyl acetate-hexane (1:8, v/v). Recrystallization from diethyl ether-hexane gave colorless prism crystals. melting point: 60-61° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hrs
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a30ca8f01b24459d93edfdc6d9f50dea
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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