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Benzyl Chloride → 4-Hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate

HRID 1439306
ノート
印刷プレビュー

反応式

HRID 1439306 の反応式
[OH:1][CH:2]([CH:4]([CH2:8][OH:9])[CH:5]([OH:7])[CH3:6])[CH3:3].[H-].[Na+].[H][H].C(Cl)C1C=CC=CC=1.Cl.[CH2:23]([NH:39][C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)[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][CH2:37][CH3:38]>C(COC)OC.CN(C)C1C=CN=CC=1.O.C(Cl)(Cl)Cl>[CH2:23]([NH:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]([O:1][CH:2]([CH:4]([CH2:8][OH:9])[CH:5]([OH:7])[CH3:6])[CH3:3])=[O:45])=[CH:47][CH:48]=1)[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][CH2:37][CH3:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 612343-(Hydroxymethyl)pentane-2,4-diolHCID 132553224-Hexadecylaminobenzoyl chloride hydrochlorideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 213269404-Hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate

試薬・触媒・溶媒

4
HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
10 °C

実験手順

A 13.4 g. of 2,4-dihydroxy-3-hydroxymethylpentane solution in dimethoxyethane is added to 2.4 g. of sodium hydride (washed free of mineral oil). After hydrogen evolution ceased, 12.65 g. of benzyl chloride is added and the mixture refluxed for 4 hours. After cooling to 10° C., 24.4 g. of 4-dimethylaminopyridine and 41.6 g. of 4-(n-hexadecylamino)benzoyl chloride hydrochloride are added. Chloroform and water are added after 16 hours and the chloroform extract is dried and evaporated to dryness. The residue is dissolved in acetic acid and hydrogenated at 30 psi hydrogen pressure over palladium block. After filtration and dilution with water, the 4-hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate is obtained as a white solid.

後処理

  1. temperaturethe mixture refluxed for 4 hours
  2. extractionthe chloroform extract
  3. customis dried
  4. customevaporated to dryness
  5. dissolutionThe residue is dissolved in acetic acid and hydrogenated at 30 psi hydrogen pressure over palladium block
  6. filtrationAfter filtration and dilution with water

出典と根拠

ORDレコード
ord-90709a3b73d541599a5ed1b0b5d4c205
出典データセット
uspto-grants-1977_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04058550

反応ノート

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