3-Methylpent-2-en-1-ol → 3-Methyl-2-Pentenyl Angelate

HRID 65318

Reaction equation

HRID 65318 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])/[C:2](=[CH:4]\[CH3:5])/[CH3:3].[CH3:9][C:10]([CH2:14]C)=[CH:11][CH2:12]O.C([O-])(=O)C.C([Sn+2]CCCCCCCC)CCCCCCC.C([O-])(=O)C>C1(C)C=CC=CC=1>[C:1]([O:7][CH2:8][CH:9]=[C:10]([CH3:14])[CH2:11][CH3:12])(=[O:6])/[C:2](=[CH:4]\[CH3:5])/[CH3:3]

Participants

5

Reactant 3

HCID 1510393-Methylpent-2-en-1-olHCID 5356352Methyl (2Z)-2-methyl-2-butenoateHCID 22386089Dioctyltin acetate

Product 1

HCID 867410343-Methyl-2-Pentenyl Angelate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 22.8 g. of methyl angelate, 10 g. of 3-methyl-2-pentenol, 80 ml. of toluene and 1 g. of dioctyltin acetate was placed in a 300 ml. glass flask, which was equipped with a Soxhlet extractor filled on the top with molecular sieve 4A and a reflux cooler. The above mixture was heated under continuous reflux while returning the refluxed liquid through the molecular sieve 4A to the flask. The mixture resulted from the heating for a total of 17 hours was subjected to single distillation to give 14.2 g. of a distillate boiling at 115° C. (22 mmHg). The distillate was further subjected to rectification to give 9.70 g. of a distillate boiling at 115° C. (22 mmHg). Analysis of the compound by gaschromatography (Column: Silicone SE-52, 2%/chromosorb GHP) indicated a purity of 99.403% in terms of the area ratio. Refractive index (D ray, 20° C.) was 1.463. Infrared spectrum (liquid film) had absorptions at 2850-3020, 1720, 1670, 1650, 1455, 1385, 1350, 1255, 1225, 1155, 1080, 1040, 960, 845 and 760 cm-1.

Workup

  1. additionA mixture of 22.8 g
  2. customglass flask, which was equipped with a Soxhlet extractor
  3. temperatureThe above mixture was heated
  4. temperatureunder continuous reflux
  5. customThe mixture resulted from the heating for a total of 17 hours
  6. distillationwas subjected to single distillation
  7. customto give 14.2 g
  8. customto give 9.70 g
  9. customRefractive index (D ray, 20° C.)

Sources & evidence

ORD record
ord-3da10889b49a415bb483b4106c634417
Source dataset
uspto-grants-1986_09
Patent number
US04613680

Linked notes

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