Acetic Acid → HCID 20358469, compound

HRID 2083489Notes

Reaction equation

HRID 2083489 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH:18]([CH3:20])[CH3:19].C[O-].[Na+].[CH:24]([C:26]([CH3:28])=[O:27])=[CH2:25].C(O)(=O)C>CO.C1C=CC=CC=1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH:18]([CH3:20])[CH3:19])[CH2:25][CH2:24][C:26](=[O:27])[CH3:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6570Methyl vinyl ketoneHCID 40499{[6,7-Dichloro-1-oxo-2-(propan-2-yl)-2,3-dihydro-1H-inden-5-yl]oxy}acetic acidHCID 10942334Sodium Methoxide

Product 1

HCID 20358469HCID 20358469, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A stirred solution of (1-oxo-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid (3.17 g., 0.01 mole) and sodium methoxide (3.2 g., 0.05 mole) in methanol (100 ml.) and benzene (100 ml.) in an inert atmosphere is cooled to 0° C. and treated with methyl vinyl ketone (2.0 g., 0.029 mole) in methanol (10 ml.) during a 1/2 hour period then stirred 72 hours at 25° C. The reaction mixture is acidified with acetic acid, evaporated to dryness, extracted with chloroform, washed with water, dried over magnesium sulfate and evaporated to dryness affording [1-oxo-2-isopropyl-2-(3-oxobutyl)-6,7-dichloro-5-indanyloxy]acetic acid which melts at 125°-128° C. after recrystallization from methanol.

Workup

  1. customevaporated to dryness
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-47fde6dbf95f4c798a076df5b4170015
Source dataset
uspto-grants-1978_04
Patent number
US04085219

Reaction notes

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