Oxygen → 11-(Methylthio)undecanoic acid

HRID 2380071

反応式

HRID 2380071 の反応式
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH3:15]I.O=O.[OH-].[Na+]>O.C(O)C>[CH3:15][S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

参加物

7

反応物 4

HCID 977OxygenHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 54350211-Mercaptoundecanoic Acid

生成物 1

HCID 34898511-(Methylthio)undecanoic acid収率 58.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Into a 3-neck round-bottom flask fitted with a condenser and an addition funnel were added 20 g of 11-mercaptoundecanoic acid, 13 g of methyl iodide and 200 mL of ethanol. A slow flow of nitrogen through the reactor was started to exclude oxygen because mercaptans can be converted into disulfides in the presence of air and strong alkali. A solution of 7.33 g of sodium hydroxide in 14.66 g of water was added dropwise to the reaction mixture via the addition funnel. Any unreacted methyl iodide, the ethanol and the water were removed using a rotovap. The residue was acidified using a mixture of concentrated hydrochloric acid and ice. After isolation the product was distilled. After a small amount of a low boiling fraction was collected, the crude product was collected at ~1 nun of Hg at 180° C. weighing 22.75 g. The crude product was distilled to yield 12.5 g of desired product representing 58.7% of theoretical based upon the weight of starting 11-mercaptoundecanoic acid.

後処理

  1. customInto a 3-neck round-bottom flask fitted with a condenser and an addition funnel
  2. customAny unreacted methyl iodide, the ethanol and the water were removed
  3. additiona mixture of concentrated hydrochloric acid and ice
  4. distillationAfter isolation the product was distilled
  5. customAfter a small amount of a low boiling fraction was collected
  6. customthe crude product was collected at ~1 nun of Hg at 180° C.
  7. distillationThe crude product was distilled

出典と根拠

ORDレコード
ord-c8a5a0360b7f49ff962833e09726e49f
出典データセット
uspto-grants-1994_11
特許番号
US05364959

関連ノート

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