Ethyl Acetate → 2-Methyl-beta-octadecyl-1,3-dioxolan-2-propanol

HRID 235707

Reaction equation

HRID 235707 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH2:13][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:15](OCC)=[O:16])[O:12][CH2:11][CH2:10][O:9]1.C(OCC)(=O)C.[OH-].[Na+]>CCOCC.O>[CH3:7][C:8]1([CH2:13][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:15][OH:16])[O:9][CH2:10][CH2:11][O:12]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 867412692-Methyl-alpha-octadecyl-1,3-dioxolan-2-propanoic acid, ethyl ester

Product 1

HCID 202189492-Methyl-beta-octadecyl-1,3-dioxolan-2-propanolYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of about 3.75 g of lithium aluminum hydride in about 100 ml of ether at about 0° C., was added dropwise, under argon, over about 20 minutes, a solution of about 29 g of 2-methyl-α-octadecyl-1,3-dioxolan-2-propanoic acid, ethyl ester in about 200 ml of ether. This mixture was stirred about 40 minutes at room temperature, then about 15 ml of ethyl acetate were added dropwise, followed by about 1.5 ml of water, about 3 ml of about 15% sodium hydroxide and about 4 ml of water. The mixture was then filtered through celite and the solid washed with ether. The solvent was removed from the filtrate, giving an oil which crystallized on standing, giving about 24.1 g of the desired title compound, mp 34°-35° C.

Workup

  1. additionwas added dropwise, under argon, over about 20 minutes
  2. filtrationThe mixture was then filtered through celite
  3. washthe solid washed with ether
  4. customThe solvent was removed from the filtrate
  5. customgiving an oil which
  6. customcrystallized

Sources & evidence

ORD record
ord-f937a14c4e2644b1b6c42cf2ce43211b
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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