Iodoacetic Acid → (1-Oxo-2,2,3-trimethyl-6,7-dichloro-5-indanyloxy)acetic Acid

HRID 1679733Notes

Reaction equation

HRID 1679733 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:10]([CH3:11])[C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([OH:12])[CH:8]=2)[C:3]1=[O:15].I[CH2:18][C:19]([OH:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:15]=[C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:12][CH2:18][C:19]([OH:21])=[O:20])=[C:6]([Cl:13])[C:5]=2[Cl:14])[CH:10]([CH3:11])[C:2]1([CH3:1])[CH3:16]

Participants

5

Reactant 3

HCID 5240Iodoacetic AcidHCID 11430Potassium CarbonateHCID 203584682,2,3-Trimethyl-5-hydroxy-6,7-dichloro1-indanone

Product 1

HCID 20358437(1-Oxo-2,2,3-trimethyl-6,7-dichloro-5-indanyloxy)acetic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,2,3-trimethyl-5-hydroxy-6,7-dichloro-1-indanone (6.1 g., 0.025 mole), iodoacetic acid (5.58 g., 0.03 mole) and potassium carbonate (4.14 g., 0.03 mole) in acetone (80 ml.) is refluxed for 20 hours. The acetone is evaporated and the residue is dissolved in water and acidified with hydrochloric acid. The (1-oxo-2,2,3-trimethyl-6,7-dichloro-5-indanyloxy)acetic acid which separates is filtered, rinsed with water and dried.

Workup

  1. temperatureis refluxed for 20 hours
  2. customThe acetone is evaporated
  3. dissolutionthe residue is dissolved in water
  4. filtrationThe (1-oxo-2,2,3-trimethyl-6,7-dichloro-5-indanyloxy)acetic acid which separates is filtered
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-0af2a9ec10dc4b26bf6adc0bb3944fc0
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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