HCID 11380534, compound → 2-Methylidenehexadecan-1-ol

HRID 638410Notes

Reaction equation

HRID 638410 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]=[C:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:13](OC)=[O:14].C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:11]=[C:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 11380534HCID 11380534, compoundHCID 21225700DiisobutylaluminumhydrideHCID 21226206Ethyl acetate hexane

Product 1

HCID 132263472-Methylidenehexadecan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diisobutylaluminum hydride in CH2Cl2 (47 ml of a 1M solution, 0.047 mole, Aldrich Chem. Co.) was stirred under nitrogen in a round-bottom flask and cooled in an ice-water bath. To this was added dropwise over a period of 4 minutes a solution of 2-methylenehexadecanoic acid, methyl ester (2.82 g, 20 mmole) in CH2Cl2 (20 ml). The reaction was complete within 30 minutes as determined by TLC (20% ethyl acetate-hexane) of a sample quenched in brine-ether. The reaction was worked up after one hour by diluting with methylene chloride (300 ml) and adding several milliliters each of methanol and water. A gelatinous mass formed which broke up upon vigorous swirling. The mixture was filtered through Celite and the filtrate dried over MgSO4. Following filtration and concentration, an oily residue was obtained. The residue crystallized and was recrystallized by dissolving in hexane at room temperature then cooling in the freezer. Crystals were collected from the cold hexane by rapid filtration. 2-Methylenehexadecan-1-ol (22) was obtained in a first crop (1.718 g) of colorless crystals, mp 33°-34° C., and a second crop (0.081 g, total 1.799 g, 0.0071 mole, 71%).

Workup

  1. temperaturecooled in an ice-water bath
  2. customquenched in brine-ether
  3. waitThe reaction was worked up after one hour
  4. additionby diluting with methylene chloride (300 ml)
  5. additionadding several milliliters each of methanol and water
  6. customA gelatinous mass formed which
  7. filtrationThe mixture was filtered through Celite
  8. dry with materialthe filtrate dried over MgSO4
  9. filtrationfiltration and concentration
  10. customan oily residue was obtained
  11. customThe residue crystallized
  12. customwas recrystallized
  13. dissolutionby dissolving in hexane at room temperature
  14. temperaturethen cooling in the freezer
  15. filtrationCrystals were collected from the cold hexane by rapid filtration

Sources & evidence

ORD record
ord-65cb00b611f54af7a81f730f8cf7cabf
Source dataset
uspto-grants-1985_12
Patent number
US04560811

Reaction notes

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