Diisobutylaluminum hydride → 3-Hexadecyloxy-2-methylenepropan-1-ol

HRID 248168Notes

Reaction equation

HRID 248168 reaction equation
[CH2:1]([O:17][CH2:18][C:19](=[CH2:25])[C:20](OCC)=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CC(C[AlH]CC(C)C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH2:1]([O:17][CH2:18][C:19](=[CH2:25])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 24436Sodium SulfateHCID 12971817Ethyl 2-[(hexadecyloxy)methyl]-2-propenoate

Product 1

HCID 113588863-Hexadecyloxy-2-methylenepropan-1-olYield 139.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 21 g of ethyl 2-[(hexadecyloxy)methyl]-2-propenoate in 400 ml of ether cooled to 0° C. under an inert atmosphere is added 2.25 ml of 1,2M DIBAL in hexanes over 30 minutes. The reaction is stirred at ambient temperature for 2 hours then cooled to 0° C. while 20 ml of saturated sodium sulfate is added dropwise. After filtering, the cake is washed with ether. The combined ether washings are dried and the solvent removed. The residue is crystallized from methyl alcohol:water to give 25.8 g of the desired product as a colorless solid.

Workup

  1. additionis added dropwise
  2. filtrationAfter filtering
  3. washthe cake is washed with ether
  4. dry with materialThe combined ether washings are dried
  5. customthe solvent removed
  6. customThe residue is crystallized from methyl alcohol

Sources & evidence

ORD record
ord-eeaa8f7dcba34274a83881da46652956
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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