Sodium Hydroxide → HCID 13613313, compound

HRID 223793Notes

Reaction equation

HRID 223793 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([O:20]C)=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH:22]=[CH2:23])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH:22]=[CH2:23])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13613309HCID 13613309, compound

Product 1

HCID 13613313HCID 13613313, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl [(5,6-dichloro-3-oxo-9a-vinyl-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetate (4.0 gm., 0.011 mole) is added to a solution composed of 20% aqueous sodium hydroxide solution (4.32 ml., 0.022 mole) and methanol (45 ml.). The mixture is stirred and heated at reflux for two hours and then concentrated in vacuo at 50° C. The residue is dissolved in water (50 ml.) and made acid to Congo red paper with 6 normal hydrochloric acid. The solid that separates is removed by filtration, washed with water, then with a little methanol and finally with a little ether. After recrystallization from acetic acid, there is obtained pure [(5,6-dichloro-3-oxo-9a-vinyl-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid.

Workup

  1. temperatureheated
  2. temperatureat reflux for two hours
  3. concentrationconcentrated in vacuo at 50° C
  4. dissolutionThe residue is dissolved in water (50 ml.)
  5. customThe solid that separates is removed by filtration
  6. washwashed with water
  7. customAfter recrystallization from acetic acid

Sources & evidence

ORD record
ord-468bcb5eb3f8493c8929b31925279515
Source dataset
uspto-grants-1982_10
Patent number
US04356313

Reaction notes

Loading…