Water → HCID 22759220, compound

HRID 460857Notes

Reaction equation

HRID 460857 reaction equation
[Na].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[C:13]([CH:16]([CH2:28][CH2:29][CH2:30][CH:31]1[O:33][CH2:32]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:15])[CH3:14].O>C(O)C.CCOCC>[C:13]([CH:16]([CH2:28][CH2:29][CH2:30][CH:31]([OH:33])[CH2:32][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:11])([F:12])[F:2])[CH:5]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 5360545SodiumHCID 22759269HCID 22759269, compound

Product 1

HCID 22759220HCID 22759220, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium (1.15 g., 0.05 mole) is dissolved in ethanol (60 ml.). 3-Trifluoromethylphenol (14.6 g., 0.09 mole) is added and then ethyl 8-acetyl-12,13-epoxytridecanoate (13.0 g., 0.0435 mole). The resulting solution is heated under reflux for 1.5 hour. It is then cooled and poured into 300 ml. of water. The oily product is taken up in ether, washed with 100 ml. of 5% sodium hydroxide solution, water and brine and dried over sodium sulfate. The ether is evaporated in vacuo leaving 17.4 g. of the title compound as a yellow oil. It is used in the next step without purification.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureunder reflux for 1.5 hour
  3. temperatureIt is then cooled
  4. additionpoured into 300 ml
  5. washwashed with 100 ml
  6. dry with materialof 5% sodium hydroxide solution, water and brine and dried over sodium sulfate
  7. customThe ether is evaporated in vacuo
  8. customleaving 17.4 g

Sources & evidence

ORD record
ord-e667d5947a244450ad0d3127302f43e4
Source dataset
uspto-grants-1977_12
Patent number
US04061643

Reaction notes

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