Potassium Carbonate → HCID 54012844, compound

HRID 1680855Notes

Reaction equation

HRID 1680855 reaction equation
[CH:1]1([C:4]([OH:6])=[O:5])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([CH2:24]Br)[CH:18]=[CH:17]2>CC(C)=O>[CH3:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([CH2:24][O:5][C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:6])[CH:18]=[CH:17]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15655Cyclopropanecarboxylic acidHCID 123373022-(Bromomethyl)-6-methylnaphthalene

Product 1

HCID 54012844HCID 54012844, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
50 °C

Procedure

1.89 g of cyclopropane carboxylic acid are dissolved in 50 ml of acetone, treated with 5.5 g of potassium carbonate and heated to 50° C. A solution of 4.7 g of 6-methyl-2-(bromomethyl)naphthalene in 20 ml of acetone is then added dropwise. The mixture is left to react at 65° C. for 15 hours. The mixture is cooled and filtered. The residue is then rinsed with acetone and the filtrate is evaporated. The residue is purified chromatography on silica gel with hexane/ethyl acetate (9:1) to yield pure cyclopropane carboxylic acid (6-methyl-2-naphthyl)methyl ester of melting point 75°-78° C. (from petane/ether).

Workup

  1. waitThe mixture is left
  2. customto react at 65° C. for 15 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washThe residue is then rinsed with acetone
  6. customthe filtrate is evaporated
  7. customThe residue is purified chromatography on silica gel with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-5635dae7c6424c1b9c7cfee98d8ce001
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

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