Acetic Anhydride → 4-(4-Nitrophenyl)oxane-2,6-dione

HRID 930131Notes

Reaction equation

HRID 930131 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(OC(=O)C)(=O)C>CCOCC>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][C:12](=[O:14])[O:18][C:16](=[O:17])[CH2:15]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 184046303-(4-Nitrophenyl)pentanedioic acid

Product 1

HCID 178879674-(4-Nitrophenyl)oxane-2,6-dioneYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 20.0 g (79.0 mmol) of 3-(4-nitro-phenyl)-pentanedioic acid (as prepared in the previous step) and 22.4 mL (237 mmol) of acetic anhydride. The mixture was heated to 80° C. for 1 h, cooled to RT, and treated slowly with ether until the product began to precipitate. After allowing the solid to fully precipitate, the solid was filtered, washed with ether, and air-dried to afford 13.0 g (70%) of the title compound as an off-white solid: 1H-NMR (CDCl3; 400 MHz): δ 8.28 (d, 2H, J=8.8 Hz), 7.41 (d, 2H, J=8.8 Hz), 3.64-3.53 (m, 1H), 3.22-3.13 (m, 2H), 2.96-2.85 (m, 2H).

Workup

  1. temperaturecooled to RT
  2. customto precipitate
  3. customto fully precipitate
  4. filtrationthe solid was filtered
  5. washwashed with ether
  6. customair-dried

Sources & evidence

ORD record
ord-2169a2128f57427681830410d2d9b589
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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