Methyl vinyl ketone → Cyclohexane ethylacetate

HRID 1873489Notes

Reaction equation

HRID 1873489 reaction equation
C([C:3]([CH3:5])=[O:4])=C.CS[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.C(N(CC)CC)C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.Cl>[CH2:8]1[CH2:15][CH2:14][CH2:11][CH2:10][CH2:9]1.[C:12]([O:4][CH2:3][CH3:5])(=[O:13])[CH3:11]

Participants

6

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 21867204Cyclohexane ethylacetateYield 53%

Reagents, catalysts & solvents 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
75 °C

Procedure

Methyl vinyl ketone (1.16 g, 0.016 mol) and p-methylsulfanylbenzaldehyde (2.4 g, 0.016 mol) were reacted in the presence of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (0.837 g, 0.0032 mol) and triethylamine (1.14 g, 0.011 mol). b) Stir the reaction mixture at 75° C. under a nitrogen atmosphere for 24 h. c) Cool the mixture to room temperature, add ice and 30 mL of concentrated HCl to the mixture until pH 2. d) Stir for 30 min. e) Extract with ethyl acetate and neutralize the combined organic fractions with an aqueous solution of NaHCO3. f) Dry the organic fraction on anhydrous sodium sulphate for 3 h. g) Purify the product by column chromatography on aluminium oxide (Brockmann grade II-III), eluting with a 3:1 cyclohexane/ethyl acetate mixture (53% yield). 1′) Alternative Method of Preparation of Compound having Formula 4a

Workup

  1. temperatureCool the mixture to room temperature
  2. stirringStir for 30 min. e)
  3. extractionExtract with ethyl acetate
  4. dry with materialf) Dry the organic fraction on anhydrous sodium sulphate for 3 h.
  5. customPurify the product by column chromatography on aluminium oxide (Brockmann grade II-III)

Sources & evidence

ORD record
ord-7b7ef1b97b83462098fee20fec11503c
Source dataset
uspto-grants-2012_11
Patent number
US08304410B2

Reaction notes

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