Ethanol → HCID 70571221, compound

HRID 1680861Notes

Reaction equation

HRID 1680861 reaction equation
[CH:1]1([C:4](Cl)=O)[CH2:3][CH2:2]1.[SH2:7].[Na].Br[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1.[OH-:21].[Na+].[CH2:23]([OH:25])[CH3:24]>ClCCl>[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[CH2:10][O:25][C:23]([C:24]1[S:7][CH:2]=[CH:1][CH:4]=1)=[O:21].[CH2:1]1[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 702EthanolHCID 14798Sodium HydroxideHCID 703202-BromomethylnaphthaleneHCID 77637Cyclopropanecarbonyl chlorideHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 70571221HCID 70571221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.6 g of cyclopropane carboxylic acid chloride are added over 5 minutes to a solution of 2.0 g of sodium hydrogen sulfide in 20 ml of ethanol which is cooled in ice. After 30 minutes, 5.5 g of 2-bromomethylnaphthalene are added. Then 10 ml of 10% sodium hydroxide are slowly added dropwise at room temperature. After 1 hour stirring at room temperature, 25 ml of dichloromethane are added and the solution is washed twice with 10% potassium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulfate and evaporated. The residue is purified by chromatography on silica gel to yield pure cyclopropane thiolcarboxylic acid 2-naphthylmethyl ester.

Workup

  1. temperatureis cooled in ice
  2. washthe solution is washed twice with 10% potassium bicarbonate solution and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0b0ac1465cd6417aaed620734439a138
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

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