Methanol → HCID 11380534, compound

HRID 2049142Notes

Reaction equation

HRID 2049142 reaction equation
[CH2:1]([C:15](=[CH2:19])[C:16]([OH:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].B(F)(F)F.[CH3:24]O>>[CH2:1]([C:15](=[CH2:19])[C:16]([O:18][CH3:24])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 6356Boron trifluorideHCID 12731441HCID 12731441, compound

Product 1

HCID 11380534HCID 11380534, compound

Procedure

14.6 Grams of 2-tetradecylacrylic acid (0.052 mole) are combined with 65 ml of absolute methanol and 15 ml of 51% BF3 in methanol in a 200 ml flask equipped with a condenser and drying tube. The system is heated under reflux for six hours (two layers appear when cooled). The mixture 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 anhydrous MgSO4. The ether solvent is removed under reduced pressure. The oily residue of methyl 2-tetradecylacrylate (14.70 g) is not purified further (>95% pure by GC) and used directly in the next step.

Workup

  1. customequipped with a condenser
  2. customdrying tube
  3. temperatureThe system is heated
  4. temperatureunder reflux for six hours
  5. temperature(two layers appear when cooled)
  6. concentrationThe mixture is concentrated to 1/2 volume
  7. extractionThe oily material is extracted with ether
  8. washwashed with water
  9. dry with materialdried over anhydrous MgSO4
  10. customThe ether solvent is removed under reduced pressure
  11. customThe oily residue of methyl 2-tetradecylacrylate (14.70 g) is not purified further (>95% pure by GC)

Sources & evidence

ORD record
ord-5da517cca00a45b781c8505a23870dc5
Source dataset
uspto-grants-1980_04
Patent number
US04196300

Reaction notes

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