2-Methyl-2-butene → HCID 11482198, compound

HRID 1797488Notes

Reaction equation

HRID 1797488 reaction equation
[CH:1]([C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH3:15])[C:6]([O:16][CH3:17])=[CH:5][CH:4]=1)=[O:2].P([O-])(O)(O)=[O:19].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O1CCCC1.O>[CH2:12]([O:11][C:9]([C:8]1[C:7]([O:14][CH3:15])=[C:6]([O:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:1]([OH:19])=[O:2])=[O:10])[CH3:13]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 610645Benzoic acid, 6-formyl-2,3-dimethoxy-, ethyl esterHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 11482198HCID 11482198, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 6-formyl-2,3-dimethoxybenzoate (5.24 g, 22 mmol), sodium dihydrogen phosphate (3.60 g, 30 mmol) and 2-methyl-2-butene (10.3 ml, 96.8 mmol) in t-butanol (20 ml), tetrahydrofuran (20 ml) and water (20 ml) was stirred at room temperature for 10 min. To the obtained mixture was added sodium chlorite (6.76 g, 74.8 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to give 2-(ethoxycarbonyl)-3,4-dimethoxybenzoic acid (4.51 g, 80.7%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-c60ced6484874ea2b4bef26ca3d679e4
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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