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Hydrochloric Acid → 3-(Octadecyloxy)-2,2-bis[(octadecyloxy)methyl]-1-propanol

HRID 1502534
ノート
印刷プレビュー

反応式

HRID 1502534 の反応式
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].Br[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][CH2:25][CH2:26][CH2:27][CH3:28].[H-].[Na+].Cl>C(Cl)(Cl)Cl.CN(C=O)C>[CH2:11]([O:1][CH2:2][C:3]([CH2:8][O:9][CH2:28][CH2:27][CH2:26][CH2:25][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][CH3:11])([CH2:6][O:7][CH2:28][CH2:27][CH2:26][CH2:25][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][CH3:11])[CH2:4][OH:5])[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][CH2:25][CH2:26][CH2:27][CH3:28]
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

7

反応物 4

HCID 313Hydrochloric AcidHCID 82181-BromooctadecaneHCID 8285PentaerythritolHCID 24758Sodium hydride

生成物 1

HCID 142519643-(Octadecyloxy)-2,2-bis[(octadecyloxy)methyl]-1-propanol収率 23%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To pentaerythritol (1.5 g, 11.0 mmol) were added DMF (100 ml), 1-bromooctadecane (11.4 g, 34.2 mmol) and sodium hydride (60 wt %, 1.54 g, 38.5 mmol), and the mixture was stirred at 100° C. for 22 hr. The reaction mixture was cooled to room temperature, chloroform (150 ml) was added, and 1N hydrochloric acid (150 ml) was added further dropwise. After stirring, the aqueous layer was removed, and the organic layer was further washed with 1N hydrochloric acid (100 ml) and water (100 ml). The organic layer was evaporated under reduced pressure, and the residue was precipitated with methanol (150 ml), and the obtained precipitate was washed with methanol (150 ml). The crude crystals were dried and purified by silica gel column chromatography (hexane:chloroform=1:1→ hexane:ethyl acetate=10:1) to give 2,2,2-tris(octadecyloxymethyl)ethanol (2.21 g, 2.47 mmol, yield 23%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringAfter stirring
  3. customthe aqueous layer was removed
  4. washthe organic layer was further washed with 1N hydrochloric acid (100 ml) and water (100 ml)
  5. customThe organic layer was evaporated under reduced pressure
  6. customthe residue was precipitated with methanol (150 ml)
  7. washthe obtained precipitate was washed with methanol (150 ml)
  8. customThe crude crystals were dried
  9. custompurified by silica gel column chromatography (hexane:chloroform=1:1→ hexane:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-a75b49562d074cbc94046e3bc8cab203
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206230B2

反応ノート

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