3-Methyl-4-penten-1-ol → 3-Methyl-4-pentenyl 2-methylisocrotonate

HRID 65319

Reaction equation

HRID 65319 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])/[C:2](=[CH:4]\[CH3:5])/[CH3:3].[CH3:9][CH:10]([CH:14]=C)[CH2:11][CH2:12]O.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCCCCCC)CCCCCCC.C([O-])(=O)CCCCCCCCCCC>C1(C)C=CC=CC=1>[C:1]([O:7][CH2:8][CH2:9][CH:10]([CH3:14])[CH:11]=[CH2:12])(=[O:6])/[C:2](=[CH:4]\[CH3:5])/[CH3:3]

Participants

5

Reactant 3

HCID 1235253-Methyl-4-penten-1-olHCID 5356352Methyl (2Z)-2-methyl-2-butenoateHCID 22292224Dioctyltin laurate

Product 1

HCID 162054563-Methyl-4-pentenyl 2-methylisocrotonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 22.8 g. of methyl angelate, 10.0 g. of 3-methyl-4-pentenol, 100 ml. of toluene and 0.9 g. of dioctyltin laurate was reacted under the same conditions as in Example 1. The resulting mixture was subjected to single distillation to give 16.91 g. of a distillate boiling at 109° C. (21 mmHg). The distillate was further subjected to rectification to give 12.54 g. of a distillate boiling at 109° C. (21 mmHg). Analysis of the compound by gaschromatography done under the same conditions as in Example 12 indicated a purity of 99.653% in terms of the area ratio. Refractive index was 1.443.

Workup

  1. additionA mixture of 22.8 g
  2. distillationThe resulting mixture was subjected to single distillation
  3. customto give 16.91 g
  4. customto give 12.54 g

Sources & evidence

ORD record
ord-2803290f8bd24e6097437ba0628ef4bc
Source dataset
uspto-grants-1986_09
Patent number
US04613680

Linked notes

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