Sulfuric Acid → 1-Octyn-3-ol, 3,6-dimethyl-

HRID 68011

반응식

HRID 68011 반응식
[CH3:1][CH:2]([CH2:8][CH3:9])[CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[C:10]([Mg]Cl)#[CH:11].S(=O)(=O)(O)O>O1CCCC1>[CH3:6][C:5]([OH:7])([CH2:4][CH2:3][CH:2]([CH3:1])[CH2:8][CH3:9])[C:10]#[CH:11]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 289655-Methyl-2-heptanoneHCID 178462451HCID 178462451, 화합물

생성물 1

HCID 1742441-Octyn-3-ol, 3,6-dimethyl-수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

128 g (1 mole) of 5-methyl-heptan-2-one are added in the course of 1 hour, with stirring, to 1 liter of a 1.1 molar solution of ethynyl-magnesium chloride in tetrahydrofuran at 10° C. After allowing about a further hour's reaction, the mixture is worked up. To do so, 2 N sulfuric acid is added, whilst cooling with ice, until two clear phases are present. The organic phase is then separated off and washed neutral with water, if necessary, and the tetrahydrofuran is distilled off at 50° C./67 mbar. The residue is subjected to fractional distillation. 143 g of main fraction, boiling at 50°-52° C./0.01 mbar, are obtained; nD25 =1.4411. This corresponds to a yield of 93%. Scent: predominantly floral, woody, herbal, minty with a spicy, slightly animal after-scent.

후처리

  1. customAfter allowing about a further hour's reaction
  2. temperaturewhilst cooling with ice, until two clear phases
  3. customThe organic phase is then separated off
  4. washwashed neutral with water
  5. distillationif necessary, and the tetrahydrofuran is distilled off at 50° C./67 mbar
  6. distillationThe residue is subjected to fractional distillation
  7. custom143 g of main fraction, boiling at 50°-52° C./0.01 mbar, are obtained

출처 및 근거

ORD 기록
ord-ec909e227fbe440faa5cc39a5bd828a5
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04347388

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