Hydrochloric Acid → 3-oxopropyl Benzoate

HRID 1709646Notes

Reaction equation

HRID 1709646 reaction equation
[C:1]([O:9][CH2:10][CH2:11][CH:12](OCC)[O:13]CC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)C>O1CCCC1>[C:1]([O:9][CH2:10][CH2:11][CH:12]=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 148558813-Ethoxy-4-oxahexyl benzoate

Product 1

HCID 110084893-oxopropyl BenzoateYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 57.0 grams (0.226 mole) of 3-ethoxy-4-oxahexyl benzoate in 475 ml of tetrahydrofuran and 475 ml of aqueous 10% hydrochloric acid was stirred at ambient temperature for 18 hours. After this time the reaction mixture was stirred with 700 ml of diethyl ether. The organic layer was separated, washed with water, and then was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure yielding 28.0 grams of 3-oxopropyl benzoate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialwas dried with sodium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a2a7d9c0faa44079367cc3f294f643e
Source dataset
uspto-grants-1990_08
Patent number
US04950666

Reaction notes

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