Phthalic Acid → Phthalic Anhydride

HRID 1028353Notes

Reaction equation

HRID 1028353 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=O.C(N(CC1C=CC=C(CN(C(C)C)C(C)C)C=1B(O)O)C(C)C)(C)C.B(O)O>CCCCCCC>[C:4]1(=[O:6])[O:12][C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Participants

5

Reactant 3

HCID 1017Phthalic AcidHCID 61668Boronic AcidHCID 58581721HCID 58581721, compound

Product 1

HCID 6811Phthalic AnhydrideYield 72%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Phthalic acid (2.5 mmol), 2,6-bis(diisopropylaminomethyl)phenylboronic acid (hereinafter, referred to as “boronic acid compound A”, 0.25 mol) as an arylboronic acid catalyst, and heptane (10 mL) as a solvent were added in a flask having a volume of 20 mL, and a column (small Soxhlet extractor) filled with dried molecular sieves 3A (approximately 3 g) was fitted to the flask. The mixture was heated for 12 hours under azeotropic reflux conditions with the removal of water. After the reaction mixture was cooled to room temperature, heptane was evaporated under reduced pressure. The crude product of phthalic anhydride thus obtained was analyzed by 1H NMR (CDCl3), and the yield thereof was calculated. When the same procedure was repeatedly performed a plurality of times, the yield was 72% to 81%.

Workup

  1. additionwere added in a flask
  2. additiona column (small Soxhlet extractor) filled
  3. dry with materialwith dried molecular sieves 3A (approximately 3 g)
  4. customwas fitted to the flask
  5. temperatureThe mixture was heated for 12 hours
  6. temperatureunder azeotropic reflux conditions
  7. customwith the removal of water
  8. customheptane was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a99e9a3fe9824723970a3666d22df5c0
Source dataset
uspto-grants-2014_05
Patent number
US08735582B2

Reaction notes

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