Chloroform → HCID 13108922, compound

HRID 1277428Notes

Reaction equation

HRID 1277428 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[CH2:17])[C:12]([O:14]CC)=[O:13].[OH-].[Na+].[CH:20](Cl)([Cl:22])[Cl:21]>>[Cl:21][C:20]1([Cl:22])[CH2:17][C:11]1([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 13108918HCID 13108918, compound

Product 1

HCID 13108922HCID 13108922, compound

Procedure

Ethyl 2-(2-naphthyl)-acrylate (3.86 g) was dissolved in chloroform (4.3 g) tetraethylbenzyl ammonium chloride (36 mg) was added and sodium hydroxide (9 ml; 50%) added dropwise over 10 minutes at room temperature. The reaction mixture was stirred for an additional 2 hours and then quenched in ice water and extracted with ether. The solvent layer was washed sequentially with water, dilute hydrachloric acid and water again, and dried over anhydrous sodium sulphate. After evaporation of the solvents, the oily residue was chromatographed on silica gel using petroleum ether(b.p. 60°-80°) methylene chloride as eluent. The main fraction, a yellow oil (4.85 g), was distilled under vacuum to yield the ethyl ester of 2,2-dichloro 1-(2-naphthyl)cyclopropanecarboxylic acid identified by its i.r. and p.m.r. spectra. This ester was hydrolysed by refluxing in a 1 N sodium hydroxide/ethanol solution. On acidification thecyclopropane acid was obtained as a solid. This was recrystallised from petroleum ether (b.p. 40°-60°)/methylene chloride to yield (0.97 g; 31%) of the acid, m.p. 154°-5° C.

Workup

  1. additionwas added
  2. customquenched in ice water
  3. extractionextracted with ether
  4. washThe solvent layer was washed sequentially with water
  5. additiondilute hydrachloric acid and water again
  6. dry with materialdried over anhydrous sodium sulphate
  7. customAfter evaporation of the solvents
  8. customthe oily residue was chromatographed on silica gel
  9. distillationThe main fraction, a yellow oil (4.85 g), was distilled under vacuum

Sources & evidence

ORD record
ord-cd34d1e5acaf4f1c94d47bd2effefe5e
Source dataset
uspto-grants-1981_07
Patent number
US04277490

Reaction notes

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