Methanol → HCID 53740698, compound

HRID 358511Notes

Reaction equation

HRID 358511 reaction equation
C([O:8][CH2:9][CH:10]=[C:11]([CH3:30])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:29])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:28])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:27])[C:24]([OH:26])=[O:25])C1C=CC=CC=1.[Li].C=CC=C.CO>O1CCCC1>[OH:8][CH2:9][CH:10]=[C:11]([CH3:30])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:29])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:28])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:27])[C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 78451,3-ButadieneHCID 3028194LithiumHCID 54037090HCID 54037090, compound

Product 1

HCID 53740698HCID 53740698, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of tetrahydrofuran was dissolved 5 g of the 16-benzyloxy-2,6,10,14-tetramethyl-2,6,10,14-hexadecatetraenoic acid obtained as described in the previous (a) section. This solution was added dropwise to the above-prepared lithium solution over a period of 30 min. The mixture was stirred for 30 min., and 1,3-butadiene was introduced into the mixture until the color of the mixture (blue) faded. To the resulting yellow colored solution was added methanol until the yellow faded. Subsequently, this was left standing to reach room temperature. The solid product thus obtained was collected on a filter, and then dissolved in water. The aqueous solution was made weakly-acidic by addition of 1N hydrochloric acid under ice-cooling, and then extracted with hexane. The extract was washed successively with water and a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The dried extract was concentrated, and the thus-obtained concentrate was purified over a silica gel column to give 3.3 g of 16-hydroxy-2,6,10,14-tetramethyl-2,6,10,14-hexadecatetraenoic acid.

Workup

  1. customobtained
  2. waitSubsequently, this was left
  3. customto reach room temperature
  4. customThe solid product thus obtained
  5. customwas collected on a filter
  6. dissolutiondissolved in water
  7. additionThe aqueous solution was made weakly-acidic by addition of 1N hydrochloric acid under ice-
  8. temperaturecooling
  9. extractionextracted with hexane
  10. washThe extract was washed successively with water
  11. dry with materiala saturated aqueous sodium chloride solution, and then dried over magnesium sulfate
  12. extractionThe dried extract
  13. concentrationwas concentrated
  14. concentrationthe thus-obtained concentrate
  15. customwas purified over a silica gel column

Sources & evidence

ORD record
ord-c5b4caba7c594cbfbab682ff0759c738
Source dataset
uspto-grants-1984_08
Patent number
US04468458

Reaction notes

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