Acetic Acid → HCID 86762528, compound

HRID 1621077Notes

Reaction equation

HRID 1621077 reaction equation
C[Mg]Cl.[CH3:4][C:5](=[C:10]([CH3:12])[CH3:11])[C:6](=[CH2:9])[CH:7]=[O:8].[C:13](O)(=O)C>C1COCC1>[CH3:4][CH:5]([CH:10]([CH3:12])[CH3:11])[C:6](=[CH2:9])[CH:7]([OH:8])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 86762529HCID 86762529, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86762528HCID 86762528, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
17.5 °C

Procedure

Methylmagnesium chloride in THF (3 M, 2.65 L) was charged into a flame-dried 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a condenser, and a dropping funnel. The reaction flask was cooled with an external bath to about 15-20° C. 3,4-Dimethyl-2-methylene-pentenal (prepared as above) (834 g) was fed over about 2-3 hours to allow the exotherm temperature at about 30-35° C. After the feeding was completed, the reaction mass was aged for about 2 hours. GC analysis determined a conversion rate of about 95%. The reaction mixture was poured into a mixture of ice and acetic acid (500 g). The organic layer was separated and washed sequentially with brine (500 mL) and sodium carbonate (5%, 300 mL), and further fractional distilled to provide 4,5-dimethyl-3-methylene-hexan-2-ol (804 g) with a boiling point of 110° C. at 60 mmHg.

Workup

  1. customfitted with a mechanical stirrer
  2. customat about 30-35° C
  3. customThe organic layer was separated
  4. washwashed sequentially with brine (500 mL) and sodium carbonate (5%, 300 mL)
  5. distillationfurther fractional distilled

Sources & evidence

ORD record
ord-7a0f9349431e4a769c537676a8d0c2a6
Source dataset
uspto-grants-2014_07
Patent number
US08772533B1

Reaction notes

Loading…