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

HRID 235707

反応式

HRID 235707 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f937a14c4e2644b1b6c42cf2ce43211b
出典データセット
uspto-grants-1987_02
特許番号
US04640913

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