2,4-Dimethyl-3-cyclohexene carboxaldehyde → α-Ethyl-2,4-dimethyl-3-cyclohexene-1-methanol

HRID 2172351Notes

Reaction equation

HRID 2172351 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][CH:6]1[CH:11]=[C:10]([CH3:12])[CH2:9][CH2:8][CH:7]1[CH:13]=[O:14]>O1CCCC1>[CH3:5][CH:6]1[CH:11]=[C:10]([CH3:12])[CH2:9][CH2:8][CH:7]1[CH:13]([OH:14])[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 933752,4-Dimethyl-3-cyclohexene carboxaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 118112370α-Ethyl-2,4-dimethyl-3-cyclohexene-1-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A reaction flask was charged with ethylmagnesium bromide solution (CH3CH2MgBr) (3 M, 2.4 L) in tetrahydrofuran (THF) and cooled to 0° C. 2,4-Dimethyl-cyclohex-3-enecarbaldehyde (905 g) was added slowly while the temperature was kept at 0° C. The reaction mixture was stirred for an additional hour and then quenched with hydrochloric acid (HCl). The reaction mixture was washed with sodium carbonate (Na2CO3) and brine. Further distillation provided 1-(2,4 -dimethyl-cyclohex-3-enyl)-propan-1-ol (1.021 Kg).

Workup

  1. customwas kept at 0° C
  2. customquenched with hydrochloric acid (HCl)
  3. washThe reaction mixture was washed with sodium carbonate (Na2CO3) and brine
  4. distillationFurther distillation

Sources & evidence

ORD record
ord-0578cbaaf9d64da2a017477a06e2d6f4
Source dataset
uspto-grants-2015_06
Patent number
US09051532B1

Reaction notes

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