Sulfuric Acid → Nerol

HRID 918558노트

반응식

HRID 918558 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[CH3:12]/[C:13](/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:14]/[C:15](OC)=[O:16].O.[OH-].[Na+]>O1CCCC1.O.C(OCC)C>[CH3:12]/[C:13](/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:14]/[CH2:15][OH:16]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 5365912Methyl nerateHCID 21226445Aluminium lithium hydrideHCID 23719242Sodium hydroxide--water (1/1/1)

생성물 1

HCID 643820Nerol

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To 10 ml. of 1 M lithium aluminum hydride in tetrahydrofuran, cooled to 0°, is added, dropwise, 0.28 ml. of 18 M sulfuric acid. The addition should be made at a rate such that the temperature remains at or below about +15°. After the addition is complete, the reaction mixture is stirred for 20 minutes and 0.55 grams of methyl (Z)-3,7-dimethylocta-2,6-dienoate is added. The reaction is allowed to proceed for about 3 hours while keeping the temperature between 0° and +5°. Then 20 ml. of ethyl ether is added, followed successively by 0.4 ml. of water, 0.4 ml. of a 15% sodium hydroxide water solution, and 1.2 ml. of water. The mixture then is filtered and the solid remaining is washed with ethyl ether. The organic filtrate is dried over sodium sulphate, filtered and evaporated under reduced pressure to yield, as an oil, (Z)-3,7-dimethylocta-2,6-dien-1-ol.

후처리

  1. additionis added
  2. additionThe addition
  3. custombelow about +15°
  4. additionAfter the addition
  5. waitto proceed for about 3 hours
  6. customthe temperature between 0° and +5°
  7. filtrationThe mixture then is filtered
  8. washthe solid remaining is washed with ethyl ether
  9. dry with materialThe organic filtrate is dried over sodium sulphate
  10. filtrationfiltered
  11. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-df4fbab709214bdfaa647e6c16a60e38
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03971827

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