Water → HCID 20080861, compound

HRID 1653840Notes

Reaction equation

HRID 1653840 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[OH2:23]>C(OC(=O)C)(=O)C>[F:1][C:2]([F:21])([F:22])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:6](=[O:23])[CH:5]=[C:4]([CH3:20])[O:18][C:16]=3[CH3:17])=[CH:11][CH:10]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 962WaterHCID 20080820HCID 20080820, compound

Product 1

HCID 20080861HCID 20080861, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

To a vigorously stirred mixture of polyphosphoric acid (60 g) and acetic anhydride (26 ml) at 90° was added over 15 min a solution of 4-(4-trifluoromethoxyphenoxy) phenylpropan-2-one (9.3 g) in acetic anhydride (30 ml). The mixture was stirred for a further 30 min at 90° then poured into water (1 liter) and extracted with toluene (2×500 ml). The combined extracts were washed with water then satd. aq. sodium bicarbonate and dried over magnesium sulphate. Concentration in vacuo gave an orange oil which was chromatographed on silica gel, eluting with dichloromethane then 1:19 methanol/dichloromethane, to give the title compound as an oil (4.1 g), NMR δH (CDCl3) 6.9-7.4 (8H, m), 6.16 (1H, s), 2.24 (3H, s), 2.16 (3H, s).

Workup

  1. extractionextracted with toluene (2×500 ml)
  2. washThe combined extracts were washed with water
  3. dry with materialaq. sodium bicarbonate and dried over magnesium sulphate
  4. concentrationConcentration in vacuo
  5. customgave an orange oil which
  6. customwas chromatographed on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c977a6da7b50420598b0afaebc7897bd
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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