HCID 89704976, compound → (1-Isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol

HRID 61324Notes

Reaction equation

HRID 61324 reaction equation
C([Mg]Cl)(C)C.[CH:6]([C:9]1([CH:17]=[O:18])[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH:10]1[CH3:16])([CH3:8])[CH3:7]>O1CCCC1>[CH:6]([C:9]1([CH2:17][OH:18])[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH:10]1[CH3:16])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 89704976HCID 89704976, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 56983930(1-Isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropylmagnesium chloride ((CH3)2HCMgCl) in tetrahydrofuran (THF) (1.6 L, 3.2 mol) was loaded into a flame-dried 5 L round bottom flask. Additional THF (1 L) was added. 1-Isopropyl-2,4-dimethyl-cyclohex-3-enecarbaldehyde (obtained as detailed above) was then fed for over 2 hours at 0° C. under nitrogen. The reaction mixture was aged at 0° C. for another 3 hours and then quenched by pouring the reaction mixture onto a sulfuric acid solution (10%) on crushed ice. The organic layer was separated, washed with sodium carbonate solution, and distilled to provide (1-isopropyl-2,4-dimethyl-cyclohex-3-enyl)-methanol.

Workup

  1. customwas then fed for over 2 hours at 0° C. under nitrogen
  2. customquenched
  3. additionby pouring the reaction mixture onto a sulfuric acid solution (10%)
  4. customon crushed ice
  5. customThe organic layer was separated
  6. washwashed with sodium carbonate solution
  7. distillationdistilled

Sources & evidence

ORD record
ord-8c68af2af581457a9ac1b265fab608e2
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Reaction notes

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