Hydrochloric Acid → HCID 90238530, compound

HRID 1478757Notes

Reaction equation

HRID 1478757 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][CH:7]([CH2:12][CH:13]=[CH2:14])[CH2:8][CH:9]1[CH2:11][CH2:10]1)C.Cl>O1CCCC1>[CH:9]1([CH2:8][CH:7]([O:6][CH2:5][CH:4]=[O:3])[CH2:12][CH:13]=[CH2:14])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90238743HCID 90238743, compound

Product 1

HCID 90238530HCID 90238530, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [2-(2,2-diethoxyethoxyl)pent-4-en-1-yl]cyclopropane (C66) (20 g, 83 mmol), aqueous hydrochloric acid (2 M, 83 mL, 166 mmol) and tetrahydrofuran (250 mL) was stirred at reflux for 1 hour. The reaction mixture was cooled to room temperature and concentrated to remove tetrahydrofuran. The aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with saturated aqueous sodium chloride solution (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford the product as a colorless oil (17 g). This material was taken directly into the following step.

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationconcentrated
  3. customto remove tetrahydrofuran
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution (3×50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da0f0000370748a3a2eeeaacac70b2bd
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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