2-Methyl-2-butene → 3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoic acid

HRID 1242384Notes

Reaction equation

HRID 1242384 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].CC(=CC)C.Cl([O-])=[O:24].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[CH2:1]([O:3][C:4]([C:5]([CH3:7])([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15]([OH:24])=[O:16])[CH3:6])=[O:17])[CH3:2]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 18766496Ethyl 2-(3-formylphenoxy)-2-methylpropanoateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 219357143-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

3.33 g (14.1 mmol) of 2-(3-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (example 55A])] was dissolved in 60 ml of tert.-butanol; 7.5 ml (70.5 mmol) of 2-methyl-2-butene was added, followed by a solution of 4.14 g (36.6 mmol) of sodium chlorite and 3.30 g (21.1 mmol) of sodium dihydrogen phosphate in 35 ml of water. After 2 hours, the reaction mixture was poured into crashed ice/EtOAc and extracted twice with EtOAc; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by recrystallisation from EtOAc/heptane to give 3.19 g of the title compound as colorless solid.

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by recrystallisation from EtOAc/heptane

Sources & evidence

ORD record
ord-c57ca1e050fa4e7db2daabf4f834cf49
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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