Acetic Anhydride → 3-Hydroxy-3'-(trifluoromethyl)acrylophenone acetate

HRID 1707050

Reaction equation

HRID 1707050 reaction equation
[Na].[OH:2][CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=[O:6].O1CCOCC1.[C:23]([O:26]C(=O)C)(=[O:25])[CH3:24]>O>[C:23]([OH:26])(=[O:25])[CH3:24].[OH:2][CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 705903703-Hydroxy-3'-(trifluoromethyl)acrylophenone sodium salt

Product 1

HCID 704778283-Hydroxy-3'-(trifluoromethyl)acrylophenone acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 12.0 g. of 3-hydroxy-3'-(trifluoromethyl)acrylophenone sodium salt in 75 ml. of dioxane and 10 ml. of acetic anhydride is stirred at room temperature for 2 hours and then poured into water. The precipitate is collected by filtration, dissolved in methylene chloride and then passed through a hydrous magnesium silicate column and crystallized from methylene chloride-hexane to give the desired product, m.p. 55°-57° C.

Workup

  1. additionA suspension of 12.0 g
  2. filtrationThe precipitate is collected by filtration
  3. dissolutiondissolved in methylene chloride
  4. customcrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-c32e3cc8f157486fa32b101490769740
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Linked notes

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