Dimethylformamide → 1-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzene

HRID 1363827Notes

Reaction equation

HRID 1363827 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](/[CH3:11])\[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9].CN(C=O)C.[H-].[Na+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:11]/[C:4](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:3]/[CH2:2][O:1][CH2:25][C:24]1[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 643820Nerol

Product 1

HCID 594447481-({[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}methyl)-4-methoxybenzeneYield 97.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

Nerol (150 g, 972 mmol) was added dropwise to a DMF (1.501) suspension of sodium hydride (60%, 38.9 g, 973 mmol) under nitrogen gas stream at room temperature. The reaction solution was stirred at room temperature for one hour and then cooled to 0° C. After tetra-n-butyl ammonium iodide (35.9 g, 97.2 mmol) was added to the reaction solution, 4-methoxybenzyl chloride (148 g, 926 mmol) was added dropwise. The reaction solution was stirred at 0° C. for one hour and then at room temperature for six hours. Water was added to the reaction solution, which was then extracted with n-heptane. After the obtained organic layer was washed with water and brine (saturated solution of sodium chloride) sequentially, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=1:0→30:1→25:1) to obtain the title compound (246.7 g) as a colorless oil.

Workup

  1. temperaturecooled to 0° C
  2. additionwas added dropwise
  3. stirringThe reaction solution was stirred at 0° C. for one hour
  4. waitat room temperature for six hours
  5. extractionwas then extracted with n-heptane
  6. washAfter the obtained organic layer was washed with water and brine (saturated solution of sodium chloride) sequentially
  7. dry with materialit was dried over anhydrous magnesium sulfate
  8. filtrationAfter the drying agent was filtered off
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=1:0→30:1→25:1)

Sources & evidence

ORD record
ord-f2e7664b2ebd416c9bddc5f9c32e2df5
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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