Dimethyl Sulfate → HCID 14793999, compound

HRID 329482Notes

Reaction equation

HRID 329482 reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:10])([CH2:6][CH2:7][CH:8]=[CH2:9])[CH3:5].[CH3:11]OS(OC)(=O)=O>O1CCCC1>[CH3:11][O:10][C:4]([CH3:5])([CH2:6][CH2:7][CH:8]=[CH2:9])[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 1401335-Hexen-2-ol, 2-methyl-

Product 1

HCID 14793999HCID 14793999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium hydride (46.8 g of a 60% oil dispersion, 1.15 mol) in tetrahydrofuran (240 mL) was added 2-methylhex-5-en-2-ol (120 g, 1.05 mol) in tetrahydrofuran (240 mL). Dimethylsulfate (75 mL, 0.79 mol) in tetrahydrofuran (120 mL) was added to the cooled (0° C.) mixture. The mixture was heated at reflux for 6 hours. Workup yielded 2-methoxy-2-methylhex-5-ene, bp40 53°-58° C. (51.36 g); NMR(CDCl3)δ1.1(s,6H), 1.5-1.6(m,2H), 2.0-2.2(m,2H), 3.2(s,3H), 4.8-5.1(m,2H), 5.7-6.0(m,1H); IR(neat) 2960, 2925, 1640, 1460, 1360, 1300, 1085 cm-1 ; MS(m/e) 43, 55, 73, 81, 95, 97, 113, 114.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours

Sources & evidence

ORD record
ord-3b77ab7aa9c6417c90b1dad32a795439
Source dataset
uspto-grants-1990_01
Patent number
US04891447

Reaction notes

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