Hydrochloric Acid → 3-oxopropyl Benzoate

HRID 1090468Notes

Reaction equation

HRID 1090468 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.O>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 962WaterHCID 148558813-Ethoxy-4-oxahexyl benzoate

Product 1

HCID 110084893-oxopropyl BenzoateYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5.0 grams (0.020 mole) of 3-ethoxy-4-oxahexyl benzoate in 100 ml of tetrahydrofuran was added 100 ml of aqueous 5% hydrochloric acid. The reaction mixture was stirred at ambient temperature for three hours, and then it was poured into 100 ml of water. The mixture was extracted with two 100 ml portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 1.9 grams of 3-oxopropyl benzoate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. extractionThe mixture was extracted with two 100 ml portions of diethyl ether
  2. dry with materialThe combined extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd469015cadf4ba0a003c8ccb7cbe40f
Source dataset
uspto-grants-1992_01
Patent number
US05081287

Reaction notes

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