Sodium Hydroxide → HCID 13613316, compound

HRID 223791Notes

Reaction equation

HRID 223791 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]([CH3:24])[CH3:23])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:25])[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]([CH3:23])[CH3:24])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:25])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57206967HCID 57206967, compound

Product 1

HCID 13613316HCID 13613316, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl [(5,6-dichloro-9a-isopropyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7yl)oxy]acetate (4.2 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 drying, the product is recrystallized from acetic acid to give pure [(5,6-dichloro-9a-isopropyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid. Using a procedure similar to that described in Example 25, except that in Step A there is substituted for the [(6,7-dichloro-2-isopropyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]acetic acid, an equimolar amount of:

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 drying
  8. customthe product is recrystallized from acetic acid

Sources & evidence

ORD record
ord-9e74565e62fc4f6b92ce854d1629e824
Source dataset
uspto-grants-1982_10
Patent number
US04356313

Reaction notes

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