(1-Oxo-1,3-dihydro-2H-inden-2-ylidene)acetic acid → (1-Oxo-indan-2-yl)-acetic acid

HRID 1768935Notes

Reaction equation

HRID 1768935 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[CH:11][C:12]([OH:14])=[O:13]>CC(O)=O.[Zn]>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 1

HCID 53400974(1-Oxo-1,3-dihydro-2H-inden-2-ylidene)acetic acid

Product 1

HCID 10954334(1-Oxo-indan-2-yl)-acetic acidYield 83.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1.9 g (0.031 mol) of zinc dust suspended in 10 mL of HOAc was added 2.3 g (0.012 mol) of the product from Step A. The reaction mixture was refluxed for 1 hour, cooled, filtered and rinsed wtih acetic acid. The acetic acid solution was poured into 200 mL of H2O and extracted with ethyl acetate (3 ×50 mL), washed with H2O (2×50 mL), dried over anhydrous magensium sulfate, filtered and concentrated under vacuum to afford 1.9 g of a yellow solid. 1H NMR (CDCl3) δ: 2.6-3.5 (m, 5H), 7.4-7.8 (m, 4H), 12.2 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. washrinsed wtih acetic acid
  5. additionThe acetic acid solution was poured into 200 mL of H2O
  6. extractionextracted with ethyl acetate (3 ×50 mL)
  7. washwashed with H2O (2×50 mL)
  8. dry with materialdried over anhydrous magensium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-837e1b1dad784cc0a945b5b78bbebdfd
Source dataset
uspto-grants-1995_01
Patent number
US05380718

Reaction notes

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