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Hydrochloric Acid → 12-Hydroxy-8-(methanesulfonyl)heptadecanoic acid

HRID 262999
ノート
印刷プレビュー

反応式

HRID 262999 の反応式
COC([C:5]([S:29]([CH3:32])(=[O:31])=[O:30])([CH2:16][CH2:17][CH2:18][CH:19]([O:25]C(=O)C)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=O.[Cl-].[Na+].CS(C)=O.Cl>O>[CH3:32][S:29]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:30])=[O:31]
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

6

反応物 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 21317603Methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate

生成物 1

HCID 2021027912-Hydroxy-8-(methanesulfonyl)heptadecanoic acid収率 110.4%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒
2 回

反応条件

温度
185 °C

実験手順

A mixture of methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate (36.7 g., 0.077 mole), sodium chloride (4.68 g., 0.08 mole), water (1 ml.) and dimethylsulfoxide (60 ml.) is heated in a bath maintained at 185° C. under nitrogen for 5 hours. The resulting reaction mixture is concentrated in vacuo at 100° C. providing an oily residue which is diluted with water. The aqueous mixture is acidified to Congo Red with 6N hydrochloric acid and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo leaving the title compound as a viscous oil (31 g., 95%), pmr (CDCl3) δ 2.0 (s, 3H), 2.82 (s, 3H), 3.63 (s, 3H) and 4.9 (b, H).

後処理

  1. temperatureis heated in a bath
  2. customThe resulting reaction mixture
  3. concentrationis concentrated in vacuo at 100° C.
  4. customproviding an oily residue which
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. washis washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-650ecb0a1bd54c7cbc26ce482de136f3
出典データセット
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04155908

反応ノート

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