Hydrochloric Acid → (1,3-Dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy)acetic acid

HRID 1659173Notes

Reaction equation

HRID 1659173 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([OH:15])=[C:8]([CH3:14])[C:9]=2[CH3:13])[C:4]1=[O:16])[CH3:2].Br[CH2:20][C:21]([O:23]CC)=[O:22].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].Cl>CN(C)C=O.CO>[O:16]=[C:4]1[C:5]2[C:10](=[C:9]([CH3:13])[C:8]([CH3:14])=[C:7]([O:15][CH2:20][C:21]([OH:23])=[O:22])[CH:6]=2)[C:11](=[O:12])[C:3]1([CH2:1][CH3:2])[CH2:17][CH3:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 215167872,2-Diethyl-6-hydroxy-4,5-dimethyl-1H-indene-1,3(2H)-dione

Product 1

HCID 21516773(1,3-Dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 2,2-diethyl-4,5-dimethyl-6-hydroxy-indan-1,3-dione (3.5 g., 0.014 mole), ethyl bromoacetate (2.7 g., 0.016 mole) and potassium carbonate (2.2 g., 0.016 mole) in dimethylformamide (20 ml.) is heated at 65°C. for 2 hours, treated with methanol (40 ml.) and potassium hydroxide (1.1 g., 0.02 mole) refluxed for 1/2 hour then poured into dilute hydrochloric acid (500 ml.) affording 4.2 g. of (1,3-dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy)-acetic acid which melts at 134°-136°C. after recrystallization from acetic acid-water.

Workup

  1. temperaturerefluxed for 1/2 hour
  2. customaffording 4.2 g
  3. customof (1,3-dioxo-2,2-diethyl-4,5-dimethyl-6-indanyloxy)-acetic acid which melts at 134°-136°C. after recrystallization from acetic acid-water

Sources & evidence

ORD record
ord-c39835ba0a334ed2b9e45dc5e044eba0
Source dataset
uspto-grants-1976_06
Patent number
US03966966

Reaction notes

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