Trifluoroacetic acid → HCID 14547226, compound

HRID 2232799Notes

Reaction equation

HRID 2232799 reaction equation
O[C:2]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][C:4]#[N:5].FC(F)(F)C(O)=O>ClCCl>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11](/[C:2](/[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:3]/[C:4]#[N:5])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14347485HCID 14347485, compound

Product 1

HCID 14547226HCID 14547226, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the above carbinol (107.8 g) in dichloromethane (540 mL) containing trifluoroacetic acid (21.6 mL) was heated at reflux for 7 hours and then was left at room tempertature overnight. The solution was washed in turn with water (250 mL). 1N NaOH solution (500 mL) and with brine (100 mL). After the aqueous layers were backwashed with dichloromethane (2×100 mL). the combined organic phases were dried (MgSO4) and evaporated to yield 99.2 g of crude (E)-3-(4-methoxyphenyl)-2-octenenitrile as an oil. The crude contained <8% of the (Z)-isomer.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. washThe solution was washed in turn with water (250 mL)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-4d363a03b0194d2bb8d49e01980b2034
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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