Hydrochloric Acid → HCID 13566084, compound

HRID 2291632Notes

Reaction equation

HRID 2291632 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl.O>C(O)(=O)C>[O:1]=[C:2]1[O:6][CH:5]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14102861HCID 14102861, compound

Product 1

HCID 13566084HCID 13566084, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-(5-oxo-4-pentyloxy-3-phenyl-2,5-dihydro-2-furyl)propionate (3 g) and 3N hydrochloric acid (28 ml) in acetic acid (28 ml) was heated at 100° C. for 2 hours with stirring. After cooling the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine successively and dried. Evaporation of the solvent gave a residue which was recrystallized from a mixture of n-hexane and ethyl acetate to give 3-(5-oxo-4-pentyloxy-3-phenyl2,5-dihydro-2-furyl)propionic acid (2.20 g).

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine successively
  4. customdried
  5. customEvaporation of the solvent
  6. customgave a residue which
  7. customwas recrystallized from a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-a379b8bbce114d6b9002d740678a9ff5
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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