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

HRID 1164553Notes

Reaction equation

HRID 1164553 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, compound

Product 1

HCID 13706918HCID 13706918, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude dibromo acid, 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 hours. 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 product, methyl 2-(7,8-dibromohexadecyl)-acrylate.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 6 hours
  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-9bc71b4bbc3648b1853d28e4453363da
Source dataset
uspto-grants-1983_01
Patent number
US04370343

Reaction notes

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