Water → HCID 20080796, compound

HRID 1653838Notes

Reaction equation

HRID 1653838 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

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 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).

Workup

  1. extractionextracted with toluene (2×500 ml)
  2. washThe combined extracts were washed with water
  3. dry with materialaq. sodium bicarbonate, dried over magnesium sulphate
  4. customevaporated
  5. customto give an oil
  6. customwas recrystallised from carbon tetrachloride

Sources & evidence

ORD record
ord-7bff8d2e4b594381b738e592b0329dba
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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