Dimethyl Sulfate → 2,6-Dimethyl-2-methoxyhept-5-ene

HRID 1088003Notes

Reaction equation

HRID 1088003 reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:12])([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH3:5].[CH3:13]OS(OC)(=O)=O>O1CCCC1>[CH3:3][C:4]([O:12][CH3:13])([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH3:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 801835-Hepten-2-ol, 2,6-dimethyl-

Product 1

HCID 147939932,6-Dimethyl-2-methoxyhept-5-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To sodium hydride (93.5 g, 3.9 mol) suspended in tetrahydrofuran (300 mL) was added 2,6-dimethylhept-5-en-2-ol (500 g, 3.5 mol) in tetrahydrofuran (1000 mL). The mixture was heated at reflux until gas evolution was complete. Dimethylsulfate (274 mL, 2.9 mol) in tetrahydrofuran (226 mL) was added to the cold (0~C) mixture. After standing for 16 h, the mixture was heated at reflux for 7 hours. Aqueous workup yielded 2,6-dimethyl-2-methoxyhept-5-ene, bp40 65-68~C (461.5 g); NMR(CDC13) 1.2(s,6H), 1.4-1.6(m,2H), 1.6(s,3H), 1.7(s,3H), 1.9-2.1(m,2H), 3.2(s,3H), 5.1-5.2(m,1H); IR(neat) 2970, 2932, 1462, 1442, 1373, 1357, 1195, 1072 cm-1 ; MS(m/e) 41, 67, 73, 109, 124, 142.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux until gas evolution
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 7 hours

Sources & evidence

ORD record
ord-9b46cabb3a924dbc8888c4247a514bf2
Source dataset
uspto-grants-1990_10
Patent number
US04960946

Reaction notes

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