Hydrochloric Acid → 1-(2-Hydroxy-5,5-dimethylcyclohexyl)pent-4-en-1-one

HRID 544812Notes

Reaction equation

HRID 544812 reaction equation
[C:1]([CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][CH:6]1[O:13]C(C)OCC)([O:3]C)=O.[CH:19]([Mg]Br)=[CH2:20].[CH:23](Br)=[CH2:24].Cl>C1COCC1.C(Cl)Cl.CCOC(C)=O>[OH:13][CH:6]1[CH2:7][CH2:8][C:9]([CH3:11])([CH3:12])[CH2:10][CH:5]1[C:1](=[O:3])[CH2:23][CH2:24][CH:19]=[CH2:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11641BromoetheneHCID 67201636HCID 67201636, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 672014931-(2-Hydroxy-5,5-dimethylcyclohexyl)pent-4-en-1-oneYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A solution of 2-carbomethoxy-4,4-dimethyl-1-(2-methyl-1,3-dioxapent-1-yl)cyclohexane (5.16 g) in 10 ml of THF was added dropwise, over 15 minutes, to a solution of vinylmagnesium bromide (1.2 g) and vinyl bromide (5.35 g) in 20 ml of THF at 65° C. After 4 hours the mixture was cooled and poured into cold 20% aqueous HCl (40 ml). Extraction of the mixture with Et2O, removal of the solvents and a SiO2 chromatography (CH2Cl2/AcOEt) provide pure 1-(2-hydroxy-5,5-dimethyl-1-cyclohexyl)-4-penten-1-one (yield 60%).

Workup

  1. temperatureAfter 4 hours the mixture was cooled
  2. extractionExtraction of the mixture
  3. customwith Et2O, removal of the solvents

Sources & evidence

ORD record
ord-c033d13ee9a64d279fa17ee08eea6686
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

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