Carbon Dioxide → 3,4-dimethoxy-2-methylbenzoic acid

HRID 906092Notes

Reaction equation

HRID 906092 reaction equation
[Mg].Br[C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([O:12][CH3:13])=[CH:5][CH:4]=1.C[Mg]Br.[C:17](=[O:19])=[O:18].Cl>O1CCCC1.O>[CH3:11][O:10][C:7]1[C:8]([CH3:9])=[C:3]([CH:4]=[CH:5][C:6]=1[O:12][CH3:13])[C:17]([OH:19])=[O:18]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8259711-bromo-3,4-dimethoxy-2-methylbenzeneHCID 5462224MagnesiumHCID 178418573HCID 178418573, compound

Product 1

HCID 117888183,4-dimethoxy-2-methylbenzoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of magnesium turnings (0.059 g, 2.40 mmol) in tetrahydrofuran (1 ml) was added a solution of 6-bromo-2,3-dimethoxy toluene (0.660 g, 2.3 mmol) in tetrahydrofuran (1 ml). The reaction was initiated by addition of methylmagnesium bromide and the solution was stirred at room temperature overnight under nitrogen. To the mixture was then added an excess of dry ice. When the addition was complete, water was added (2 ml) followed by 1.5 M hydrochloric acid to pH 2. The water phase was extracted with ethyl acetate (2×5 ml) and the combined organic layers were dried over sodium sulfate, filtered and concentrated to give 3,4-dimethoxy-2-methylbenzoic acid (0.315 g, 70% yield). MS (EI) for C10H12O4: 195 (M−H).

Workup

  1. additionWhen the addition
  2. extractionThe water phase was extracted with ethyl acetate (2×5 ml)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81dfe62ff2c04032b87700d7fbfd9e89
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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