Sulfuric Acid → Nerol

HRID 918558Notes

Reaction equation

HRID 918558 reaction equation
[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]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 53659122,6-Octadienoic acid, 3,7-dimethyl-, methyl ester, (2Z)-HCID 21226445Aluminium lithium hydrideHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 643820Nerol

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-df4fbab709214bdfaa647e6c16a60e38
Source dataset
uspto-grants-1976_07
Patent number
US03971827

Reaction notes

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