Sodium Chlorite → 2-Cyclopropyl-6-ethyl-benzoic acid

HRID 1950909Notes

Reaction equation

HRID 1950909 reaction equation
[CH:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:5]=2[CH:6]=[O:7])[CH2:3][CH2:2]1.Cl([O-])=[O:15].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.CC(=CC)C.O>[CH:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:5]=2[C:6]([OH:15])=[O:7])[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 589519652-Cyclopropyl-6-ethyl-benzaldehyde

Product 1

HCID 580628792-Cyclopropyl-6-ethyl-benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

2-Cyclopropyl-6-ethyl-benzaldehyde (CAS 945408-11-7) (500 mg, 2.9 mmol) was dissolved in 3.5 mL tert butanol and 1.7 mL 2-methyl-2-butene. At 0° C. a solution of sodium chlorite (80% purity, 422 mg, 3.8 mmol) and sodium dihydrogenphosphate (452 mg, 3.8 mmol) in 3 mL water was added slowly. The reaction mixture was stirred at room temperature over night. The solvents were evaporated off. The residue was taken up in 1N sodium hydroxide solution and was extracted with tert butyl methylether. The aqueous phase was adjusted at pH 1 with 25% HCl and extracted twice with tert butyl methylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was used without any further purification, white solid (412 mg, 75%), MS: m/e=189.3 [(M−H)−].

Workup

  1. customThe solvents were evaporated off
  2. extractionwas extracted with tert butyl methylether
  3. extractionextracted twice with tert butyl methylether
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was used without any further purification, white solid (412 mg, 75%), MS

Sources & evidence

ORD record
ord-fd3978e2430d4230acee5963576eccba
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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