Hydrochloric Acid → 4,4-Dimethylcyclohexane-1-carbaldehyde

HRID 70266Notes

Reaction equation

HRID 70266 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][C:5](=[CH:8][O:9]C)[CH2:4][CH2:3]1.Cl>C1COCC1.C(OCC)C.[Cl-].[Na+].O.O>[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH:5]([CH:8]=[O:9])[CH2:4][CH2:3]1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 589086674-Methoxymethylene-1,1-dimethyl-cyclohexane

Product 1

HCID 222352954,4-Dimethylcyclohexane-1-carbaldehyde

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (4,4-dimethyl cyclohexylidene)methyl methyl ether (6.7 g, 0.043 mol) in THF (200 mL) containing 6M HCl (aq) (60 mL) was stirred at room temperature for 24 hr. The reaction mixture was diluted with a mixture of ethyl ether, hexanes, brine and water. The mixture was separated and the aqueous phase was extracted with ethyl ether. The combined organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo, affording 4,4-dimethylcyclohexanecarbaldehyde as a yellow oil, used without further purification.

Workup

  1. customThe mixture was separated
  2. extractionthe aqueous phase was extracted with ethyl ether
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdff3e5f4670424e8ceb6362f31354bf
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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