Water → HCID 19363476, compound

HRID 850419Notes

Reaction equation

HRID 850419 reaction equation
[Cr](O)(O)(=O)=O.[CH3:6][C:7]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])([CH3:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH2:23]>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:14][C:7]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]([OH:23])=[O:19])([CH3:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 24425Chromic AcidHCID 19363337HCID 19363337, compound

Product 1

HCID 19363476HCID 19363476, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent2×

Procedure

Chromic acid (105.4 mg, 1.05 mmol, 1.2 eq) was dissolved in acetic acid (2 ml), and a solution of 3-(1,1-dimethylheptyl)benzaldehyde (205 mg, 0.878 mmol) in acetic acid (2 ml) was added to the solution under ice-cooling, which was followed by stirring for 2 minutes. The mixture was further stirred at room temperature for 30 minutes. Conc. sulfuric acid (2 drops) was added, and the mixture was stirred for 3 hours. To this reaction mixture, water (10 ml) was added, and the mixture was extracted twice with ethyl acetate (10 ml). The organic layers were combined, washed with saturated brine (20 ml), and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=2/1) to give 3-(1,1-dimethylheptyl)benzoic acid (205 mg, 99.0%).

Workup

  1. temperaturecooling
  2. stirringThe mixture was further stirred at room temperature for 30 minutes
  3. stirringthe mixture was stirred for 3 hours
  4. extractionthe mixture was extracted twice with ethyl acetate (10 ml)
  5. washwashed with saturated brine (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4bda2c9eb0f1437993d4130cd36aa522
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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