Phosphoric Acid → HCID 15195204, compound

HRID 2417368Notes

Reaction equation

HRID 2417368 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-was
  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-e525b3056e5b43489f18d80a0c7ad5ed
Source dataset
uspto-grants-2004_11
Patent number
US06825371B2

Reaction notes

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