1-Dodecanol → 3-Dodecyloxy-4-methylthiophene

HRID 2106898Notes

Reaction equation

HRID 2106898 reaction equation
[CH3:1][O:2][C:3]1[C:7]([CH3:8])=[CH:6][S:5][CH:4]=1.[CH2:9](O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]C.OS([O-])(=O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3]1[C:7]([CH3:8])=[CH:6][S:5][CH:4]=1)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 516919Sodium BisulfateHCID 130618593-Methoxy-4-methylthiophene

Product 1

HCID 144732153-Dodecyloxy-4-methylthiophene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

40 g of 3-methoxy-4-methylthiophene were dissolved in 120 cm3 of toluene together with 120 g of 1-dodecanol, and the solution was refluxed with 2 g of NaHSO4. 19 ml of a methanol/toluene mixture were separated off over a period of 3 hours. The solution was washed with water until neutral, dried over MgSO4 and subsequently fractionated. At 141° to 143° C. and 0.013 mbar, 55.6 g of 3-dodecyloxy-4-methylthiophene distilled over. 97% pure by GC, which corresponds to 63% of the theoretical yield. The substance was characterized by mass spectrum and 1H-NMR.

Workup

  1. custom19 ml of a methanol/toluene mixture were separated off over a period of 3 hours
  2. washThe solution was washed with water until neutral,
  3. dry with materialdried over MgSO4
  4. distillationAt 141° to 143° C. and 0.013 mbar, 55.6 g of 3-dodecyloxy-4-methylthiophene distilled over

Sources & evidence

ORD record
ord-aeff5f66a7504c1db375d246c8fcc000
Source dataset
uspto-grants-1990_06
Patent number
US04931568

Reaction notes

Loading…