2-Methyl-2-butene → HCID 21942607, compound

HRID 1167316Notes

Reaction equation

HRID 1167316 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:11][O:12][CH3:13])[CH:10]=1)[C:6]#[N:7])=[O:2].CC(=CC)C.Cl([O-])=[O:20].[Na+]>C(O)(C)(C)C.O>[C:6]([C:5]1[CH:4]=[C:3]([CH:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=1)[C:1]([OH:20])=[O:2])#[N:7]

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 22996180HCID 22996180, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 21942607HCID 21942607, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a reaction mixture of 3-formyl-5-methoxymethyl-benzonitrile (128 mg, 0.73 mmol) in tert-butyl alcohol (3 mL) and water (1.5 mL) were added 2-methyl-2-butene (1.5 mL) and sodium chlorite (198 mg, 80% technical grade, dissolved in 1.5 mL of water), respectively. The resulting mixture was stirred at room temperature for 5 h then partitioned between water and methylene chloride. The aqueous layer was extracted with methylene chloride. The organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to dryness to afford 3-cyano-5-methoxymethyl-benzoic acid (90 mg, 64%).

Workup

  1. customthen partitioned between water and methylene chloride
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-55cb74b5b78e4659ab055eea8324e53f
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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