ChemicalBook CAS DataBase List Tropolone

Tropolone synthesis

7synthesis methods

Product Name:Tropolone
CAS Number:533-75-5
Molecular formula:C7H6O2
Molecular Weight:122.12

To a mixture of sodium hydroxide (33 g) with glacial acetic acid (270 ml) was added dropwise via funnel 7,7-dichlorobicyclo[3,2,0]hepta-2-ene-6-ketone (33.5 g) under nitrogen, and the mixture was heated to reflux for 8 hours. After PH was adjusted to 1 with hydrochloric acid (50 ml), the mixture was filtered and extracted with benzene (3 × 90ml). The combined extracts were concentrated in vacuo to give brownish black oil.Fraction of reduced pressure distillation at 100 °C/67 Pa was collected to give gross product as a pale yellow solid. Recrystallization from mixture of dichloromethane and pentane (1/4, V/V) gave analytically pure product Tropolone(17.8 g,77%) as a white needle crystal, m.p. 50~51 °C.

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Yield:-

Steps:

Multi-step reaction with 3 steps
1: polymerization inhibitor; nitrogen / 470 °C
2: 700 °C / 2 - 5 Torr
3: acetic acid; potassium acetate / 120 - 130 °C

References:

Drysdale et al. [Journal of the American Chemical Society,1958,vol. 80,p. 3672]

5307-99-3 Synthesis