Phenacyl bromide → HCID 54398312、化合物

HRID 728745ノート

反応式

HRID 728745 の反応式
[CH2:1]([CH:15]([CH2:19][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]CCCC)[C:16]([OH:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:39](Br)[C:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:41].C(N(CC)CC)C.[O:56]1CCCC1>>[OH:56][CH:19]([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][CH3:34])[CH:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:16]([O:18][CH2:39][C:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:41])=[O:17]

参加物

5

反応物 4

HCID 6259Phenacyl bromideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 21275969HCID 21275969、化合物

生成物 1

HCID 54398312HCID 54398312、化合物収率 33%

実験手順

3-Hydroxy-2-n-tetradecyl-octadecanoic acid (II) prepared as described [Bulletin de la Societe chimique de France 504-510 (1954)] was dissolved in dry tetrahydrofuran (45 ml), and then phenacyl bromide (2.70 g, 13.59 millimole) and triethyl amine (1.89 ml, 13.59 millimole) were successively added thereto with ice cooling. The mixture was allowed to warm to the room temperature, and reacted for 23 hours. The insoluble mass in the reaction mixture was filtered off with suction and the solvent was distilled from the filtrate. The residue was dissolved in benzene and the obtained solution was fractionated through silicagel column chromatography (benzene). After the fractions comprising impurities were discarded, the later colorless fractions were pooled, and the solvent was distilled off from the fraction to, give white crystals of phenacyl 3-hydroxy-2-n-tetradecyl-octadecanoate (IV) (1.81 g, yield 33%).

後処理

  1. customreacted for 23 hours
  2. filtrationThe insoluble mass in the reaction mixture was filtered off with suction
  3. distillationthe solvent was distilled from the filtrate
  4. dissolutionThe residue was dissolved in benzene
  5. distillationthe solvent was distilled off from the fraction to,

出典と根拠

ORDレコード
ord-454e7029a4b6401f8956e1f4d5ed1225
出典データセット
uspto-grants-1991_09
特許番号
US05049664

反応ノート

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