Potassium Hydroxide → cis-2-[(6,7-Dihydroxy-5,6,7,8-tetrahydro-1-naphthyl)oxy]-2-methylpropionic acid

HRID 267557Notes

Reaction equation

HRID 267557 reaction equation
[OH:1][C@H:2]1[C@@H:11]([OH:12])[CH2:10][C:9]2[C:8]([O:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:3]1.[OH-].[K+]>CO>[OH:1][C@H:2]1[C@@H:11]([OH:12])[CH2:10][C:9]2[C:8]([O:13][C:14]([CH3:21])([CH3:20])[C:15]([OH:17])=[O:16])=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86733119cis-2-[(6,7-Dihydroxy-5,6,7,8-tetrahydro-1-naphthyl)oxy]-2-methylpropionic acid, ethyl ester

Product 1

HCID 68138405cis-2-[(6,7-Dihydroxy-5,6,7,8-tetrahydro-1-naphthyl)oxy]-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.05 mole of the product of Example 1 in 50 ml. of methyl alcohol, 30 ml. of 40% methanolic potassium hydroxide is added and the mixture is refluxed for 0.5 hours. The solvent is removed in vacuo, the residue dissolved in water, acidified and extracted with chloroform. The chloroform extract is washed with water, dried and concentrated to give the title compound as a thick oil.

Workup

  1. temperaturethe mixture is refluxed for 0.5 hours
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue dissolved in water
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7df46420488b4e109710f45015a8066e
Source dataset
uspto-grants-1976_03
Patent number
US03943149

Reaction notes

Loading…