Hydrochloric Acid → HCID 14986480, compound

HRID 488146Notes

Reaction equation

HRID 488146 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:22]COC)=[C:6]([O:20][CH3:21])[CH:7]=[C:8]2/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2].Cl.O>C(O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:22])=[C:6]([O:20][CH3:21])[CH:7]=[C:8]2/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 10427605HCID 10427605, compound

Product 1

HCID 14986480HCID 14986480, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.3 g of ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)propenoate in ethanol (10 ml) was added 1 ml of concentrated hydrochloric acid and stirred at room temperature for 2 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After evaporation, hexane was added for crystallization to obtain 0.76 g of the titled compound as pale yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporation, hexane
  5. additionwas added for crystallization

Sources & evidence

ORD record
ord-52c64705e2db4388aeed1bb1621d63a6
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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