Iodine → HCID 11063406, compound

HRID 1680856Notes

Reaction equation

HRID 1680856 reaction equation
[Mg].II.[CH2:4](Br)[CH:5]=[CH2:6].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH:18]=[O:19]>C(OCC)C>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH:18]([OH:19])[CH2:6][CH:5]=[CH2:4]

Participants

6

Reactant 4

HCID 807IodineHCID 62012-NaphthalenecarboxaldehydeHCID 7841Allyl bromide2×HCID 5462224Magnesium

Product 1

HCID 11063406HCID 11063406, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3.28 g of magnesium are treated with an iodine crystal and covered with absolute diethyl ether. The reaction is started by the addition of 2 g of allyl bromide. A mixture of 19.78 g of allyl bromide and 15.62 g of 2-naphthaldehyde in absolute diethyl ether is then added dropwise to maintain the mixture at reflux. After the addition is completed, the mixture is left to stir at room temperature overnight. The mixture is poured into an ice - 2 N hydrochloric acid solution and extracted three times with ether. The ether extracts are washed with water and saturated sodium chloride solution, dried over sodium sulfate and evaporated to yield 1-(2-naphthyl)-3-buten-1-ol which can be used without further purification for the reaction with cyclopropane carboxylic acid chloride in the process of Example 2. The resulting product is cyclopropane carboxylic acid 1-(2-naphthyl)-3-butenyl ester, m.p. 35°-39° C.

Workup

  1. additionis then added dropwise
  2. temperatureto maintain the mixture
  3. temperatureat reflux
  4. additionAfter the addition
  5. waitthe mixture is left
  6. extractionextracted three times with ether
  7. washThe ether extracts are washed with water and saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-8b4d467e31764921ad7834388a6b0eaa
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

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