Acetic Anhydride → HCID 18355513, compound

HRID 1637801Notes

Reaction equation

HRID 1637801 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]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]([OH:43])=O)=[CH:36][CH:35]=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:41](=[O:43])[C:40]=2[C:37]2[CH:36]=[CH:35][C:34]([F:33])=[CH:39][CH:38]=2)=[CH:13][CH:14]=1)(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 282356(2-Hydroxy-4-methoxyphenyl)(4-hydroxyphenyl)methanone

Product 1

HCID 18355513HCID 18355513, 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-fluorophenyl 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, and saturated sodium chloride solution, then dried over sodium sulfate and evaporated to give a yellow/orange solid, which was recrystallised from 2:1 ethanol/water (600 ml) to give the product as an off-white 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, and 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 2:1 ethanol/water (600 ml)

Sources & evidence

ORD record
ord-d550b863f3a5443d8c49dbc229c9453d
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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