Acetic Anhydride → HCID 18355491, compound

HRID 1602744Notes

Reaction equation

HRID 1602744 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=O.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(N(CC)CC)C.[F:33][C:34]([F:46])([F:45])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]([OH:44])=O)=[CH:37][CH:36]=1>C(OCC)(=O)C.O>[C:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:3]3[C:2](=[CH:7][C:6]([O:8][CH3:9])=[CH:5][CH:4]=3)[O:1][C:42](=[O:44])[C:41]=2[C:38]2[CH:37]=[CH:36][C:35]([C:34]([F:33])([F:46])[F:45])=[CH:40][CH:39]=2)=[CH:13][CH:14]=1)(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 282356(2-Hydroxy-4-methoxyphenyl)(4-hydroxyphenyl)methanone

Product 1

HCID 18355491HCID 18355491, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (2-hydroxy-4-methoxyphenyl)-(4-hydroxyphenyl)-methanone (7.33 g, 30.0 mmol), acetic anhydride (15 ml), triethylamine (5.5 ml, 39.5 mmol), and 4-(trifluoromethyl)phenyl acetic acid (4.63 g, 30.0 mmol) was stirred at 135° C. for 18 h, and the resulting orange coloured solution poured into water (120 ml) and stirred for 3 h. The resulting mixture of aqueous solution plus sticky solid was diluted with ethyl acetate (300 ml) to dissolve the solid, and the organic layer separated. The aqueous phase was further extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with water, saturated sodium chloride solution, dried over sodium sulfate and evaporated to give a yellow/orange solid, which was recrystallised from 6:1 ethanol/water (350 ml) to give the product as a colourless solid, which was vacuum dried.

Workup

  1. stirringstirred for 3 h
  2. additionThe resulting mixture of aqueous solution plus sticky solid
  3. dissolutionto dissolve the solid
  4. customthe organic layer separated
  5. extractionThe aqueous phase was further extracted with ethyl acetate (2×100 ml)
  6. washThe combined organic extracts were washed with water, saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give a yellow/orange solid, which
  10. customwas recrystallised from 6:1 ethanol/water (350 ml)

Sources & evidence

ORD record
ord-45ba24995bd5479498ad7dd002ac9cbe
Source dataset
uspto-grants-1999_11
Patent number
US05985306

Reaction notes

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