Acetic Acid → (2-Methyl-1H-inden-3-yl)acetic acid

HRID 437317Notes

Reaction equation

HRID 437317 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.C([CH2:14][C:15]([OH:17])=[O:16])#N.C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([C:3]=1[CH2:14][C:15]([OH:17])=[O:16])=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9740Cyanoacetic acidHCID 2492622-MethylindanoneHCID 517165Ammonium Acetate

Product 1

HCID 14419403(2-Methyl-1H-inden-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Methylindanone (0.112 mole), cyanacetic acid (10.5 g., 0.123 mole), acetic acid (6.6 g.), and ammonium acetate (1.7 g.) in dry toluene (15.5 ml.) was refluxed with stirring for 21 hrs., as the liberated water was collected in a Dean Stark trap. The toluene was concentrated and the residue dissolved in 60 ml. of hot ethanol and 14 ml. of 2.2 N aqueous potassium hydroxide solution. 22 g. Of 85% KOH in 150 ml. of water was added and the mixture refluxed for 13 hr. under N2. The ethanol was removed under vacuum, 500 ml. water added, the aqueous solution washed well with ether and then boiled with charcoal. The aqueous filtrate was acidified to pH 2 with 50% hydrochloric acid, cooled and the precipitate of 2-methylinden-3-acetic acid was collected.

Workup

  1. custom, as the liberated water was collected in a Dean Stark trap
  2. concentrationThe toluene was concentrated
  3. dissolutionthe residue dissolved in 60 ml
  4. additionof water was added
  5. temperaturethe mixture refluxed for 13 hr
  6. customThe ethanol was removed under vacuum, 500 ml
  7. additionwater added
  8. washthe aqueous solution washed well with ether
  9. temperaturecooled
  10. customthe precipitate of 2-methylinden-3-acetic acid was collected

Sources & evidence

ORD record
ord-6a7ee9c64f9e463eaa42d63efb564ed9
Source dataset
uspto-grants-1977_06
Patent number
US04030994

Reaction notes

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