Hydrochloric Acid → HCID 9974775, compound

HRID 654715Notes

Reaction equation

HRID 654715 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:20]=[C:21](/[CH3:27])\[C:22]([O:24]CC)=[O:23])[C:6]2[C:11]([C:12]=1[O:13][CH2:14][O:15][CH3:16])=[C:10]([CH2:17][CH2:18][CH3:19])[CH:9]=[CH:8][CH:7]=2.[OH-].[K+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:20]=[C:21](/[CH3:27])\[C:22]([OH:24])=[O:23])[C:6]2[C:11]([C:12]=1[O:13][CH2:14][O:15][CH3:16])=[C:10]([CH2:17][CH2:18][CH3:19])[CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11726764HCID 11726764, compound

Product 1

HCID 9974775HCID 9974775, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

170 g of ethyl (Z)-3-(3-methoxy-4-methoxymethoxy-5-propyl-1-naphthyl)-2-methylpropenoate was dissolved in 850 ml of ethanol and a potassium hydroxide aqueous solution (potassium hydroxide 60 g/water 120 ml) was added, followed by refluxing for 1 hour. After cooling to 10° C., 2.5N hydrochloric acid was added to make it pH~5, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant crystals were filtered to obtain 151 g of the titled compound as 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. concentrationconcentrated in vacuo
  6. filtrationThe resultant crystals were filtered

Sources & evidence

ORD record
ord-c74fad69b147490fa527c85a1c02f8f2
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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