Water → Acetic acid, ((4-(3-furanylcarbonyl)-1-naphthalenyl)oxy)-

HRID 1701715Notes

Reaction equation

HRID 1701715 reaction equation
[C:1]1([O:11][CH2:12][C:13]([O:15]CC)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[OH2:24]>C(O)C>[O:24]1[CH:3]=[CH:2][C:1]([C:18]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:2][CH:3]=2)=[O:21])=[CH:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 1482829Ethyl [(naphthalen-1-yl)oxy]acetate

Product 1

HCID 3052164Acetic acid, ((4-(3-furanylcarbonyl)-1-naphthalenyl)oxy)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 g of the ester obtained according to (a) are dissolved in 300 ml ethanol; after addition of 7.6 g potassium carbonate in solution in 25 ml water, the mixture is refluxed for 17 hours and the alcohol removed under reduced pressure. The residue is purified by dissolution in water; the final product is extracted from the aqueous phase after acidification. 12 g of the acid which, after recrystallisation from dichloroethane, melts at 177° C. are obtained.

Workup

  1. temperaturethe mixture is refluxed for 17 hours
  2. customthe alcohol removed under reduced pressure
  3. customThe residue is purified by dissolution in water
  4. extractionthe final product is extracted from the aqueous phase after acidification
  5. custom12 g of the acid which, after recrystallisation from dichloroethane, melts at 177° C.
  6. customare obtained

Sources & evidence

ORD record
ord-703fd5c5c37843c7b538caf41730490b
Source dataset
uspto-grants-1980_03
Patent number
US04195093

Reaction notes

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