Ethyl Acetate → 1,3-Indandione

HRID 1578455Notes

Reaction equation

HRID 1578455 reaction equation
[H-].[Na+].[C:3]1([C:18]([O:20]CC)=O)[C:4](C(OCC)=O)=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[CH:10]C=C2.C(OCC)(=[O:25])C>>[C:18]1(=[O:20])[C:3]2[C:12](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:11](=[O:25])[CH2:10]1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21894257Diethyl naphthalene-1,2-dicarboxylate

Product 1

HCID 118151,3-Indandione

Procedure

To a 50% dispersion of sodium hydride in mineral oil (4.55 g) was added to a solution of diethyl naphthalene 1,2-dicarboxylate (18.5 g) in ethyl acetate (22 ml.) and the mixture refluxed for 3.5 hrs. on a steam bath. After cooling the precipitated orange solid was filtered and decarboxylated with hydrochloric acid (35 ml.) in water (350 ml) at 70°C over 7 mins. to yield benze(e) indane-1,3-dione, m.p. (benzene) 178°C (decomp.) (Found: C, 79.21; H, 4.22; C13H8O2 requires: C, 79.58; H, 4.11%).

Workup

  1. temperaturethe mixture refluxed for 3.5 hrs
  2. temperatureAfter cooling the precipitated orange solid
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-aad7a1c26f3441bbaa14453854dbb96b
Source dataset
uspto-grants-1976_02
Patent number
US03936504

Reaction notes

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