Sulfuric Acid → Nerol

HRID 918558ノート

反応式

HRID 918558 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 643820Nerol

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-df4fbab709214bdfaa647e6c16a60e38
出典データセット
uspto-grants-1976_07
特許番号
US03971827

反応ノート

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