Chloroform → HCID 2780296, compound

HRID 449906Notes

Reaction equation

HRID 449906 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH:10]([Cl:13])(Cl)[Cl:11].[OH-].[Na+]>[Cl-].C[N+](C)(C)C.O>[Cl:11][C:10]1([Cl:13])[CH2:3][CH:2]1[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 15458tert-Butyl acrylate

Product 1

HCID 2780296HCID 2780296, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

Tert-butyl acrylate (32 g, 0.25 mol), CHCl3 (318 g, 3 mol), tetramethyl ammonium chloride (0.75 g, 0.0050 mol) and 50% aqueous NaOH (300 mL) were stirred at 45-50° C. for 8 hours. The mixture was diluted with water (400 mL) and the organic layer was separated. The aqueous layer was extracted with CHCl3 (75 mL). The combined organic extracts were washed with 1N HCl (200 mL) and water (250 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product was distilled to give tert-butyl 2,2-dichlorocyclopropanecarboxylate as colorless oil (16 g, yield: 30%). 1H-NMR (500 MHz, CDCl3,): δ 2.48 (m, 1H), 2.00 (m, 1H), 1.81 (m, 1H), 1.52 (s, 9H).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with CHCl3 (75 mL)
  3. washThe combined organic extracts were washed with 1N HCl (200 mL) and water (250 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-8b506d1f2ac54fdab0a2e5c6ca785edf
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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