Acetic Anhydride → 2,5-Cyclohexadien-1-one, 4-(acetyloxy)-4-phenyl-

HRID 857071Notes

Reaction equation

HRID 857071 reaction equation
[OH:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][C:5](=[O:8])[CH:4]=[CH:3]1.[C:15](OC(=O)C)(=[O:17])[CH3:16].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1.CCOCC>[C:15]([O:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=[CH:4][C:5](=[O:8])[CH:6]=[CH:7]1)(=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1795501-Hydroxy[1,1'-biphenyl]-4(1H)-one

Product 1

HCID 4827022,5-Cyclohexadien-1-one, 4-(acetyloxy)-4-phenyl-Yield 62%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-hydroxy-4-phenyl-2,5-cyclohexadienone (0.335 g, 1.8 mmol), acetic anhydride (0.276 g, 2.7 mmol, 1.5 equivalents) and triethylamine (0.273 g, 2.7 mmol, 1.5 equivalents) dissolved in dichloromethane (20 mL) was added 4-dimethylaminopyridine (DMAP) (0.044 g, 0.36 equivalents). The reaction mixture was stirred for 24 hours at room temperature, washed with 1 M HCl (20 mL) then saturated sodium hydrogen carbonate solution (2×20 mL) and the organic layer dried over magnesium sulphate. Removal of the solvent in vacuo gave an oil which was dissolved in ether, filtered and the solvent removed in vacuo to gave the title compound as a white solid. The yield was 62%; mp 100–101° C. (lit. 106–109° C.); 1H NMR (CDCl3) δ 7.48–7.36 (5H, m, ArH); 6.99 (2H, d, J 19.2 Hz, H-3, H-5); 6.36 (2H, d, J 10.2 Hz, H-2, H-6); 2.22 (3H, s, O2CCH3).

Workup

  1. washwashed with 1 M HCl (20 mL)
  2. dry with materialsaturated sodium hydrogen carbonate solution (2×20 mL) and the organic layer dried over magnesium sulphate
  3. customRemoval of the solvent in vacuo
  4. customgave an oil which
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-80969bdbb4ef4231ba05bb687b22d310
Source dataset
uspto-grants-2006_12
Patent number
US07144893B2

Reaction notes

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