Sulfuric Acid → 11-bromoundec-10-ynoic Acid

HRID 485292

반응식

HRID 485292 반응식
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[Br:14][O-].[Na+].Br[O-].BrBr.OS(O)(=O)=O>[OH-].[Na+]>[Br:14][C:11]#[C:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:13])=[O:12]

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 24408BromineHCID 3103910-Undecynoic acidHCID 5460626HypobromiteHCID 23673712Sodium hypobromite

생성물 1

HCID 411287611-bromoundec-10-ynoic Acid

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

실험 절차

To a solution of 36.45 g (200 mmol) of 10-undecynoic acid in 200 ml 1N NaOH at 0° C. was added a solution of alkaline sodium hypobromite dropwise over 30 minutes, maintaining the temperature below 5° C. (the hypobromite solution was prepared by the dropwise addition of 35.16 g (220 mmol) of bromine to 55 ml of 20N NaOH at 0°-5° C.). The mixture was stirred four hours at 0°-5° C., and was then acidified to pH 1 with 9M H2SO4. The solution was extracted with three 150 ml portions of ether. The combined extracts were dried (Na2SO4) and evaporated yielding 50.159 (96% crude) of a pale yellow solid. This was used without further purification.

후처리

  1. extractionThe solution was extracted with three 150 ml portions of ether
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated
  4. customyielding 50.159 (96% crude) of a pale yellow solid
  5. customThis was used without further purification

출처 및 근거

ORD 기록
ord-d7cb6e6fbdc8408b8fd13af33f73c559
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536450

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