Benzene → HCID 53812327, compound

HRID 1576996Notes

Reaction equation

HRID 1576996 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([CH3:19])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([CH3:16])[CH3:15])C.C1C=CC=CC=1>O>[CH3:19][C:6]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([CH3:16])[CH3:15])=[CH:5][CH2:4][OH:3]

Participants

4

Reactant 2

HCID 241Benzene2×HCID 54398367HCID 54398367, compound

Product 1

HCID 53812327HCID 53812327, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 65 g. of 3,7,10,11-tetramethyl-2,6,10-dodecatrienoic acid ethyl ester in 270 ml. of absolute benzene there was added in a period of one hour under ice cooling, 68 ml. of a 70% by weight benzene solution of sodium dihydro-bis-(2-methoxyethoxy-aluminate). This addition was carried out dropwise. After this addition, the reaction mixture was allowed to stand for one hour at room temperature under constant stirring. The reaction solution is broken up by the addition of water while it is cooled with ice. After the addition of water, the reaction mixture is filtered and poured over a saturated aqueous sodium chloride solution. The resulting reaction mixture is then exhaustively extracted with benzene. The combined benzene extracts are washed several times with water, dried over sodium sulfate and evaporated. Distillation yields pure 3,7,10,11-tetramethyl-2,6,10-dodecatrien-1-ol, b.p. 94°-96°C.10.03 mmHg; nD20 = 1.4946.

Workup

  1. additionThis addition
  2. additionAfter this addition
  3. temperatureis cooled with ice
  4. filtrationthe reaction mixture is filtered
  5. additionpoured over a saturated aqueous sodium chloride solution
  6. customThe resulting reaction mixture
  7. extractionis then exhaustively extracted with benzene
  8. washThe combined benzene extracts are washed several times with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. distillationDistillation

Sources & evidence

ORD record
ord-b211abddf80548ee8c9f431ab93d7eb0
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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