Phosphoric Acid → HCID 15195204, compound

HRID 1250849Notes

Reaction equation

HRID 1250849 reaction equation
P(=O)(O)(O)O.COC([C:10]1[C:19]2[C:13]([CH:14]=[CH:15][C:16]([CH:20]([CH3:22])[CH3:21])=[CH:17][CH:18]=2)=[CH:12][C:11]=1[CH3:23])=O.[OH-].[Na+]>>[CH3:23][C:11]1[CH:12]=[C:13]2[C:19](=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:15]=[CH:14]2)[CH:10]=1

Participants

4

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 22634768Methyl 2-methyl-6-(propan-2-yl)azulene-1-carboxylate

Product 1

HCID 15195204HCID 15195204, compoundYield 75%

Conditions

Temperature
100 °C

Procedure

70 ml of phosphoric acid was added to 3.93 g (16.2 mmol) of 1-methoxycarbonyl-2-methyl-6-isopropylazulene, and the mixture was heated at 100° C. for one hour. The resultant reaction solution was added to 300 ml of an aqueous solution containing 30 g of sodium hydroxide and extracted with hexane. An organic phase of the extract was dried with magnesium sulfate, and the solvent remaining therein was removed under a reduced pressure. The obtained crude product was filtered through silica gel. Further, the solvent contained in the filtered solid component was removed, thereby obtaining 2.23 g of 2-methyl-6-isopropylazulene (yield: 75%).

Workup

  1. customThe resultant reaction solution
  2. extractionextracted with hexane
  3. dry with materialAn organic phase of the extract was dried with magnesium sulfate
  4. customthe solvent remaining therein was removed under a reduced pressure
  5. customThe obtained crude product
  6. filtrationwas filtered through silica gel
  7. customwas removed

Sources & evidence

ORD record
ord-878c5f4a1fb64feb86eb0b36746bb817
Source dataset
uspto-grants-2002_01
Patent number
US06340652B1

Reaction notes

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