Potassium Hydroxide → HCID 21569136, compound

HRID 1579828Notes

Reaction equation

HRID 1579828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([OH:19])[C:14]([O:16]CC)=[O:15])[CH:7]=[CH:6]2.[OH-].[K+]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([OH:19])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21569133HCID 21569133, compound

Product 1

HCID 21569136HCID 21569136, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.144 moies of ethyl 6-methoxy-2-naphthylglycolate dissolved in 220 ml. of isopropanol is added 38 g. (0.7 mole) of potassium hydroxide. This mixture is then heated at reflux temperature in a nitrogen atmosphere. The solution is concentrated in vacuo to a viscous oil, which is then dissolved in 500 ml. of water and filtered. The filtrate is acidified with 10% HCl and the precipitate is taken up in ether. The ether layer is dried, filtered and the filtrate concentrated to dryness. Recrystallization of residue from benzenecyclohexane 1:1 gives 6-methoxy-2-naphthylglycolic acid.

Workup

  1. temperatureThis mixture is then heated
  2. temperatureat reflux temperature in a nitrogen atmosphere
  3. concentrationThe solution is concentrated in vacuo to a viscous oil, which
  4. dissolutionis then dissolved in 500 ml
  5. filtrationof water and filtered
  6. dry with materialThe ether layer is dried
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated to dryness
  9. customRecrystallization of residue from benzenecyclohexane 1:1

Sources & evidence

ORD record
ord-0d24fbaa333b437fa8f21c0d8b76d128
Source dataset
uspto-grants-1976_01
Patent number
US03931269

Reaction notes

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