Myristyl bromide → HCID 59467739, compound

HRID 1013856

Reaction equation

HRID 1013856 reaction equation
[H-].[Na+].[CH2:3]([O:6][CH2:7][CH:8]([OH:11])[CH2:9][OH:10])[CH:4]=[CH2:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1C=CC=CC=1.[O-][Mo]([O-])(=O)=O>[CH2:3]([O:6][CH2:7][CH:8]([O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:9][O:10][CH2:15][CH:14]=[CH2:13])[CH2:4][CH2:5][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16]

Participants

6

Reactant 3

HCID 8208Myristyl bromideHCID 24758Sodium hydrideHCID 78950Glyceryl Allyl Ether

Product 1

HCID 59467739HCID 59467739, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 24621Molybdate ionSolvent

Procedure

Benzene (250 ml) was added to 95% sodium hydride (11.4 g, 450.0 mmol), and the flask was flushed with nitrogen and sealed. A solution of 3-allyloxy-1,2-propanediol (6.6 g, 50.0 mmol) in benzene (75 ml) was added to the flask. Using a syringe, 97% 1-bromotetradecane (36.7 ml, 120.0 mmol) was added to the flask and the reaction was left to reflux overnight under a constant stream of nitrogen. Once cooled to room temperature, the excess sodium hydride was slowly quenched with ethanol until no further effervescence was observed. The solution was transferred to a separatory funnel with benzene (250 ml) and washed with distilled water (3×200 ml). The organic layer was dried with magnesium sulfate and the solvent removed on the rotary evaporator to yield a colourless oil. TLC (5% ether-hexane, developed in Molybdate) indicated that most of the starting material had reacted to form product. This resulting product was further purified by flash column chromatography (1-5% ether-hexane) to yield 15.0 g (57.3%) of 1,2-dimyristyloxy-3-allyloxypropane 1.

Workup

  1. customthe flask was flushed with nitrogen
  2. customsealed
  3. waitthe reaction was left
  4. temperatureto reflux overnight under a constant stream of nitrogen
  5. customthe excess sodium hydride was slowly quenched with ethanol until no further effervescence
  6. customThe solution was transferred to a separatory funnel with benzene (250 ml)
  7. washwashed with distilled water (3×200 ml)
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. customthe solvent removed on the rotary evaporator
  10. customto yield a colourless oil
  11. customhad reacted
  12. customto form product
  13. customThis resulting product was further purified by flash column chromatography (1-5% ether-hexane)

Sources & evidence

ORD record
ord-78f6cd138a874c35b99ab6c5d74dfe3b
Source dataset
uspto-grants-2011_07
Patent number
US07982027B2

Linked notes

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