Sodium Hydroxide → 2-Ethyl-3-carboxy-benzo[b]thiophene

HRID 436006

반응식

HRID 436006 반응식
[OH-].[Na+].BrBr.[CH2:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[C:16](=[O:18])C)[CH3:6].S(=O)(O)[O-:20].[Na+]>O1CCOCC1.O>[CH2:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[C:16]([OH:18])=[O:20])[CH3:6]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 214550882-Ethyl-3-acetyl-benzo[b]thiopheneHCID 23665763Sodium Bisulfite

생성물 1

HCID 214550892-Ethyl-3-carboxy-benzo[b]thiophene수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

반응 조건

온도
0 °C

실험 절차

Into a one-litre flask equipped with a mechanical stirrer and a dropping-funnel were introduced 39 g (0.97 mol) of sodium hydroxide with 270 ml of water. The solution was cooled to 0° C by means of an ice-bath and 20 ml (0.333 mol) of bromine were then added through the dropping-funnel followed by 190 ml of dioxan, care being taken to maintain the temperature at 0° C. Finally, still at the same temperature, a solution of 22.6 g (0.111 mol) of 2-ethyl-3-acetyl-benzo[b]thiophene in 25 ml of dioxan were introduced drop-by-drop. The mixture was then allowed to return to room temperature and stirring was maintained for 2 hours. A solution of sodium bisulphite was then added and the reaction medium was acidified and extracted with ether. The organic phase was washed with water, dried and evaporated to dryness to give 20.2 g of 2-ethyl-3-carboxy-benzo[b]thiophene. Yield 92%; M.P. 136° C.

후처리

  1. customInto a one-litre flask equipped with a mechanical stirrer and a dropping-funnel
  2. temperatureto maintain the temperature at 0° C
  3. customto return to room temperature
  4. temperaturewas maintained for 2 hours
  5. extractionextracted with ether
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b31d435d497f4e3fbccbea2599042cdf
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04007204

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