Sodium Hydroxide → 2-Ethylazulene

HRID 2417367Notes

Reaction equation

HRID 2417367 reaction equation
C([C:3]1[C:12]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[C:5](C(O)=O)[C:4]=1[CH2:16][CH3:17])#N.[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:16]([C:4]1[CH:3]=[C:12]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11]2)[CH:5]=1)[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22634765HCID 22634765, compound3×

Product 1

HCID 125714202-EthylazuleneYield 67%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

3.7 g (16.4 mmol) of the above-obtained 1-cyano-2-ethylazulene-3-carboxylic acid was separated into two parts, i.e., about 1 g and a remaining part. 30 ml of 75% sulfuric acid was added to the first part, i.e., about 1 g of 1-cyano-2-ethylazulene-3-carboxylic acid and heated to 90° C., and thereafter gradually supplied with the remaining part of 1-cyano-2-ethylazulene-3-carboxylic acid. The mixture was heated at 90° C. for 2 hours and further at 120° C. for 2 hours. The obtained reaction solution was added to an aqueous solution containing 35 g of sodium hydroxide and extracted with a mixed solution of hexane and ethyl acetate. An organic phase of the extract was removed under a reduced pressure. The resultant crude product was purified by silica gel column chromatography, to obtain 1.71 g of 2-ethyl azulene (yield: 67%)

Workup

  1. temperatureThe mixture was heated at 90° C. for 2 hours and further at 120° C. for 2 hours
  2. customThe obtained reaction solution
  3. additionwas added to an aqueous solution
  4. extractionextracted with a mixed solution of hexane and ethyl acetate
  5. customAn organic phase of the extract was removed under a reduced pressure
  6. customThe resultant crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f09d6317a49425da3505209f60f6f6b
Source dataset
uspto-grants-2004_11
Patent number
US06825371B2

Reaction notes

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