Boron, trifluoro(methanol)-, (T-4)- → HCID 13706918, compound

HRID 2163131Notes

Reaction equation

HRID 2163131 reaction equation
[Br:1][CH:2]([CH:14]([Br:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[CH2:13])[C:10]([OH:12])=[O:11].[CH3:24]O.B(F)(F)F>CO>[Br:1][CH:2]([CH:14]([Br:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[CH2:13])[C:10]([O:12][CH3:24])=[O:11]

Participants

4

Reactant 2

HCID 11062313Boron, trifluoro(methanol)-, (T-4)-HCID 13706917HCID 13706917, compound2×

Product 1

HCID 13706918HCID 13706918, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The dibromo acid product obtained in Example V, 2-(7,8-dibromohexadecyl)-acrylic acid, is dissolved in 50 ml of methanol and 5 ml of boron trifluoride methanol solution is added. The solution is heated under reflux for 6 hrs. The solution is concentrated to 1/2 volume and the acid is neutralized with saturated NaHCO3 solution to about pH 7. The oily material is extracted with ether, washed with water and dried over Na2SO4. The ether solvent is removed under reduced pressure to give 4.80 g of crude oily product, methyl 2-(7,8-dibromohexadecyl)-acrylate.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 6 hrs
  3. concentrationThe solution is concentrated to 1/2 volume
  4. extractionThe oily material is extracted with ether
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customThe ether solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5f094791533c4cf9910b94672c2e8c08
Source dataset
uspto-grants-1979_01
Patent number
US04132719

Reaction notes

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