Phosphoric Acid → 1-Methylazulene

HRID 1982173Notes

Reaction equation

HRID 1982173 reaction equation
C[C:2]1[C:11]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[C:4]([CH2:12]C(O)=O)[CH:3]=1.P(=O)(O)(O)O>>[CH3:12][C:4]1[C:5]2[C:11]([CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:2][CH:3]=1

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 23317596HCID 23317596, compound

Product 1

HCID 1366111-MethylazuleneYield 90.1%

Procedure

5.91 g of compound B is dissolved in 60 ml. of phosphoric acid and the mixture is heated (90°-80° C.) on a water bath for 15 minutes. After cooling the mixture is poured into 300 ml of ice-water and extracted with n-hexane. The organic layer is separated, washed with water, dried over anhydrous sodium sulfonate and fractionated by silicagel column chromatography using benzene as eluent to give 3.72 g (90.1%) of the objective compound.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with n-hexane
  3. customThe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfonate and fractionated by silicagel column chromatography

Sources & evidence

ORD record
ord-01555fc9b4e541318c1b8380d419267f
Source dataset
uspto-grants-1986_06
Patent number
US04595694

Reaction notes

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