Potassium Hydroxide → 6-[(7-Ethyl-3-methylnona-2,6-dien-1-yl)oxy]-2,3-dihydro-1-benzofuran

HRID 1414818Notes

Reaction equation

HRID 1414818 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[OH-].[K+].Br[CH2:14][CH:15]=[C:16]([CH3:25])[CH2:17][CH2:18][CH:19]=[C:20]([CH2:23][CH3:24])[CH2:21][CH3:22].[OH-].[Na+]>O1CCCC1.CN(C)C=O>[CH2:23]([C:20]([CH2:21][CH3:22])=[CH:19][CH2:18][CH2:17][C:16]([CH3:25])=[CH:15][CH2:14][O:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1)[CH3:24]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 540586431-Bromo-7-ethyl-3-methylnona-2,6-diene

Product 1

HCID 541803096-[(7-Ethyl-3-methylnona-2,6-dien-1-yl)oxy]-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

10.9 g. of 6-hydroxy-2,3-dihydrobenzofuran are dissolved in 80 ml. of anhydrous dimethylformamide and treated, while stirring and with ice cooling at 0° C. with 5.3 g. of freshly powdered potassium hydroxide. The mixture is stirred for 1 hour at 0° C. under a nitrogen atmosphere and then added dropwise within 1 hour to a solution of 19.6 g. of 1-bromo-7-ethyl-3-methyl-2,6-nonadiene in 10 ml. of absolute tetrahydrofuran. The mixture is allowed to stir for 2 hours at 0° C. and for 2 hours at room temperature and then poured onto a mixture of 100 ml. of 10% by weight aqueous sodium hydroxide and 100 ml. of ice-water. The mixture is extracted three times with pentane, the extracts are washed successively with 10% by weight aqueous sodium hydroxide, water and saturated sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/diethyl ether (19:1 parts by volume) there is obtained pure 6-[(7-ethyl-3-methyl-2,6-nonadienyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 132° C./0.02 mmHg; nD20 = 1.5350.

Workup

  1. stirringThe mixture is stirred for 1 hour at 0° C. under a nitrogen atmosphere
  2. additionadded dropwise within 1 hour to a solution of 19.6 g
  3. stirringto stir for 2 hours at 0° C. and for 2 hours at room temperature
  4. additionpoured onto a mixture of 100 ml
  5. extractionThe mixture is extracted three times with pentane
  6. washthe extracts are washed successively with 10% by weight aqueous sodium hydroxide, water and saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-ebe33c4bfaf4434f8c26504baf519318
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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