Thioglycerol → (+/-)-1-S-hexadecylthioglycerol

HRID 977278ノート

反応式

HRID 977278 の反応式
[SH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[OH-].[K+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:25]([S:1][CH2:2][CH:3]([CH2:4][OH:5])[OH:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

参加物

5

反応物 3

HCID 7291ThioglycerolHCID 82131-BromohexadecaneHCID 14797Potassium Hydroxide

生成物 1

HCID 13002863(+/-)-1-S-hexadecylthioglycerol収率 950.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a stirred solution of 40.0 grams (0.037 mole) 3-mercapto-1,2-propanediol in 300 milliliters of 95% ethanol, 24.9 grams (0.44 mole) of KOH was added under an inert atmosphere of nitrogen. Then, a solution of 135.0 grams (0.44 mole) bromohexadecane in 100 milliliters of 95% ethanol was added dropwise over a one-hour period, and the reaction allowed to proceed at room temperature with vigorous stirring for 24 hours. The precipitate was filtered, taken up in one liter of boiling methanol and cooled to 0° Centigrade for twelve hours. The precipitate was filtered and allowed to air dry, producing 117 grams (95%) of product (mp 72°-74° Centigrade).

後処理

  1. customto proceed at room temperature
  2. filtrationThe precipitate was filtered
  3. temperaturecooled to 0° Centigrade for twelve hours
  4. filtrationThe precipitate was filtered
  5. customto air dry

出典と根拠

ORDレコード
ord-2f81c92e4dc44e7cb7e04f2b12e41f15
出典データセット
uspto-grants-1997_03
特許番号
US05614548

反応ノート

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