Acetic Anhydride → Homophthalic anhydride

HRID 2170121Notes

Reaction equation

HRID 2170121 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=O.C(OC(=O)C)(=O)C>>[C:1]1(=[O:12])[O:13][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 66643Homophthalic acid

Product 1

HCID 12801Homophthalic anhydride

Conditions

Temperature
80 °C

Procedure

A 100 mL round-bottomed flask containing a stirring bar was charged with homophthalic acid (2.0 g, 11.101 mmol). Acetic anhydride (25.0 mL) was added, the flask was fitted with a condenser and the reaction mixture was heated at 80° C. for 2 h. The excess acetic anhydride was removed in vacuo and the solid obtained was triturated with Et2O (10.0 mL), filtered and dried to obtain homophthalic anhydride as an off white solid (1.53 g, 85%). Spectral data for this compound were consistent with those in the literature. M.p. 140-144° C. (lit. m.p. 140-145° C.); 1H NMR (400 MHz, DMSO-d6): δ=8.05 (d, J=8.2 Hz, 1H), 7.75 (app. t, 1H), 7.52 (app. t, 1H), 7.44 (d, J=7.8 Hz, 1H), 4.27 (s, 2H).

Workup

  1. additionA 100 mL round-bottomed flask containing a stirring bar
  2. customthe flask was fitted with a condenser
  3. customThe excess acetic anhydride was removed in vacuo
  4. customthe solid obtained
  5. customwas triturated with Et2O (10.0 mL)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-b6b8cb9a941e446a9d950b103363e5d5
Source dataset
uspto-grants-2015_06
Patent number
US09050586B2

Reaction notes

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