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

HRID 2163132Notes

Reaction equation

HRID 2163132 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-f0e1592950f840d290b6dbffac9768a8
Source dataset
uspto-grants-1979_01
Patent number
US04132720

Reaction notes

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