Hydrochloric Acid → 4-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoic acid

HRID 502397Notes

Reaction equation

HRID 502397 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].CC(=CC)C.Cl([O-])=[O:22].[Na+].P([O-])(O)(O)=O.[Na+].Cl>C(O)(C)(C)C.O>[CH3:1][O:2][C:3]([C:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:22])=[O:14])=[CH:11][CH:12]=1)([CH3:6])[CH3:5])=[O:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 25111210Methyl 2-(4-formylphenyl)-2-methylpropanoate

Product 1

HCID 251112114-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoic acidYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

5.60 g (27 mmol) of 2-(4-formyl-phenyl)-2-methyl-propionic acid methyl ester was dissolved in 112 mL of tert-butanol; 16.97 mL (11.20 g=136 mmol) of 2-methyl-2-butene was added, followed by a solution of 7.98 g (71 mmol) of sodium chlorite and 6.35 g (41 mmol) of sodium dihydrogen phosphate in 56 mL of water. After 20 hours, the reaction mixture was poured into crashed ice/EtOAc, the pH was adjusted to ˜3.0 with aq. HCl (1N) and it was extracted twice with EtOAc; the organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by recrystallisation from EtOAc/heptane to give 3.00 g of the title compound as colorless solid. MS: 221.2 [(M−H)−].

Workup

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

Sources & evidence

ORD record
ord-fb8a04261e1c4582a81f6620c36992fc
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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