Hydrochloric Acid → 3,7-Dimethyl-1,6-octadien-3-yl 3(beta-naphthyl)-3-oxo-2-methylpropionate

HRID 634591Notes

Reaction equation

HRID 634591 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13](=[O:28])[CH2:14][C:15]([O:17][C:18]([CH3:27])([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:19]=[CH2:20])=[O:16].[CH3:29]I.Cl>O1CCCC1>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13](=[O:28])[CH:14]([CH3:29])[C:15]([O:17][C:18]([CH3:27])([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:19]=[CH2:20])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10991722(+/-)-Linalyl (2-naphthoyl)acetate

Product 1

HCID 219325063,7-Dimethyl-1,6-octadien-3-yl 3(beta-naphthyl)-3-oxo-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (3.92 g, 0.098 mol, 60%) and tetrahydrofuran (100 mL) are placed into a 250 mL three-necked round-bottomed flask fitted with a magnetic stirrer, ice bath, addition funnel, internal thermometer and argon inlet. The contents of the flask are cooled to 0° C. 3,7-Dimethyl-1,6-octadien-3-yl 3-(β-naphthyl)-3-oxo-propionate (15.28 g, 0.044 mol) dissolved in 50 mL of tetrahydrofuran is added dropwise to the flask over 30 min. During addition, the mixture evolves gas. After stirring for 1 h, methyl iodide (10.65 g, 0.075 mol) is added to the reaction mixture. Stirring continues for 2 h at 0° C. and then at room temperature for 18 h. The mixture is neutralized with 20% HCl and extracted with diethyl ether. The organic layers are washed with saturated NaHCO3 solution, water, dried over MgSO4, filtered, concentrated by rotary evaporation and purified by flash chromatography to yield the desired compound. Structure is confirmed my 1H and 13C NMR.

Workup

  1. customfitted with a magnetic stirrer, ice bath, addition funnel
  2. additionis added dropwise to the flask over 30 min
  3. additionDuring addition
  4. stirringStirring
  5. waitcontinues for 2 h at 0° C.
  6. waitat room temperature for 18 h
  7. extractionextracted with diethyl ether
  8. washThe organic layers are washed with saturated NaHCO3 solution, water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation
  12. custompurified by flash chromatography

Sources & evidence

ORD record
ord-45458b724a0b4df4b2c1f3909ba7b38b
Source dataset
uspto-grants-2001_02
Patent number
US06184188B2

Reaction notes

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