Water → Ethyl 11-hydroxy-3,7,11-trimethyldodeca-2,4-dienoate

HRID 918312Notes

Reaction equation

HRID 918312 reaction equation
O.[O:2]1CCCC1.[CH3:7][C:8](/[CH:15]=[CH:16]/[CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[BH4-].[Na+]>[OH-].[Na+]>[OH:2][C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20][CH2:19][CH:18]([CH3:25])[CH2:17][CH:16]=[CH:15][C:8]([CH3:7])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86733725trans Ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate

Product 1

HCID 54480983Ethyl 11-hydroxy-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a mixture of 1.9 g. of mercuric acetate, 6 ml. of water and 20 ml. of tetrahydrofuran is added 1.49 g. of trans ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate slowly. After addition is complete, the reaction mixture is stirred for about 20 minutes. The mixture is cooled to about 0° and 6 ml. of aqueous sodium hydroxide (3 molar) is added followed by 0.49 g. of sodium borohydride in aqueous sodium hydroxide (about 3 molar). The mixture is stirred for about 30 minutes. The mixture is then decanted, concentrated, diluted with water and then extracted with ether. The ethereal extract is washed with water, dried over magnesium sulfate and the product chromatographed on silica gives ethyl 11-hydroxy-3,7,11-trimethyldodeca-2,4-dienoate (trans).

Workup

  1. additionTo a mixture of 1.9 g
  2. additionAfter addition
  3. temperatureThe mixture is cooled to about 0°
  4. stirringThe mixture is stirred for about 30 minutes
  5. customThe mixture is then decanted
  6. concentrationconcentrated
  7. additiondiluted with water
  8. extractionextracted with ether
  9. extractionThe ethereal extract
  10. washis washed with water
  11. dry with materialdried over magnesium sulfate
  12. customthe product chromatographed on silica

Sources & evidence

ORD record
ord-f2d28bfb571b43f386da1dfeae8c026b
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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