Water → HCID 20080796, compound

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.O.CC[O:22][CH2:23][CH3:24].[C:25](OC(=O)C)(=O)[CH3:26]>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:23](=[O:22])[CH:24]=[C:25]([CH3:26])[O:16][C:14]=3[CH3:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 962Water

HCID 3283Diethyl Ether

HCID 7918Acetic Anhydride2×

HCID 18000323HCID 18000323, compound

Product 1

HCID 20080796HCID 20080796, compound

Procedure

A solution of 4-(4-chlorophenoxy)phenylpropan-2-one (26 g) in acetic anhydride (100 ml) was added, over 5 min, to a vigorously stirred mixture of polyphosphoric acid (200 g) and acetic anhydride (100 ml) at 80°. After stirring for 30 min the mixture was poured into water (1 liter) and extracted with toluene (2×500 ml). The combined extracts were washed with water then satd. aq. sodium bicarbonate, dried over magnesium sulphate and evaporated to give an oil. Trituration with ether gave a yellow solid, which was recrystallised from carbon tetrachloride to afford the title compound (14.64 g), m.p. 150°-152°, NMR δH (CDCl3) 6.95-7.4 (8H, m), 6.2 (1H, s), 2.3 (3H, s), 2.2 (3H, s).