Water → HCID 20080908, compound

HRID 1653839Notes

Reaction equation

HRID 1653839 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.O.CC[O:25][CH2:26][CH3:27].[C:28](OC(=O)C)(=O)[CH3:29]>>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:26](=[O:25])[CH:27]=[C:28]([CH3:29])[O:17][C:15]=3[CH3:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 7918Acetic Anhydride2×HCID 20080804HCID 20080804, compound

Product 1

HCID 20080908HCID 20080908, compound

Procedure

A solution of 1-(4-(4-trifluoromethylphenoxy)phenyl)propan-2-one (54.5 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 warm mixture was poured into water (1 liter). The solution was stirred for 30 min then extracted with toluene (3×500 ml). The combined extracts were washed with water then satd. aq. sodium bicarbonate, dried over magnesium sulphate and concentrated in vacuo to give an oil. Trituration with ether afforded the title compound as a yellow solid (18.20 g), m.p. 86°-7°, NMR δH (CDCl3) 6.95-7.8 (8H, m), 6.2 (1H, s), 2.3 (3H, s), 2.2 (3H, s).

Workup

  1. stirringThe solution was stirred for 30 min
  2. extractionthen extracted with toluene (3×500 ml)
  3. washThe combined extracts were washed with water
  4. dry with materialaq. sodium bicarbonate, dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-ac2c7963bbc64396a8dee11c9ce745cb
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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