Hydrochloric Acid → (E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acid

HRID 488128Notes

Reaction equation

HRID 488128 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:23]COC)=[C:6]([O:21][CH3:22])[CH:7]=[C:8]2/[CH:13]=[C:14](\[CH3:20])/[C:15]([O:17]CC)=[O:16])[CH3:2].[OH-].[K+].Cl>C(O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:23])=[C:6]([O:21][CH3:22])[CH:7]=[C:8]2/[CH:13]=[C:14](\[CH3:20])/[C:15]([OH:17])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 9975669ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate

Product 1

HCID 6509859(E)-3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-2-methylpropenoic acidYield 102.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28 g of ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate was dissolved in 240 ml of ethanol and a potassium hydroxide aqueous solution (potassium hydroxide 28 g/water 55 ml) was added, followed by refluxing for 1 hour. 280 ml of 2N hydrochloric acid was added to the reaction mixture at ice bath temperature to make it acidic, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Diisopropyl ether was added to the resultant residue and the resultant crystals were filtered to obtain 23 g of the titled compound as pale yellow crystals.

Workup

  1. temperatureby refluxing for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. additionDiisopropyl ether was added to the resultant residue
  7. filtrationthe resultant crystals were filtered

Sources & evidence

ORD record
ord-3fc249752cb64d8eacf6d3ff841003f7
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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