Oxygen → 11-(Methylthio)undecanoic acid

HRID 1084289

반응식

HRID 1084289 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 34898511-(Methylthio)undecanoic acid수율 58.7%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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 mm 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.

후처리

  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 mm of Hg at 180° C.
  7. distillationThe crude product was distilled

출처 및 근거

ORD 기록
ord-e056294faf58454b8bb2558941a3754a
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004558

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