Sulfuric Acid → HCID 58107373, compound

HRID 78958

Reaction equation

HRID 78958 reaction equation
[CH:1]1([CH2:7][C:8](=[O:14])[CH2:9][C:10](OC)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15](Cl)[C:16](=C)[CH3:17].C[O-].[Na+].[OH-].[Na+].S(=O)(=O)(O)O>CO.O.C1(C)C=CC=CC=1>[CH:1]1([CH2:7][C:8](=[O:14])[CH2:9][CH2:10][C:16]([CH3:17])=[CH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 112413-Chloro-2-methyl-1-propeneHCID 14798Sodium HydroxideHCID 539146Methyl beta-oxocyclohexanebutanoateHCID 10942334Sodium Methoxide

Product 1

HCID 58107373HCID 58107373, compoundYield 60.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

A 250 ml flask was charged with 15.0 g of methyl 4-cyclohexyl-3-oxobutanoate (96% GC, 1 molar equivalent) and 9.8 g of methallyl chloride (1.5 molar equivalent). The mixture was heated to 70° C. and over the course of 90 minutes 13 g of a 30% solution of sodium methylate in methanol (1 molar equivalent) was added. Stirring was continued for 30 minutes and then 50 g of toluene was added. Within 1 hour 19.3 g of a 30% aqueous sodium hydroxide solution was added and stirring continued for 1 hour. After cooling to 25° C., 28.4 g of a 50% aqueous sulfuric acid solution was added over the course of 1 hour. To the slurry 70 g toluene and 40 g water were added and after decantation, the aqueous phase was drained. After concentration the crude product was fractionated leading to 8.9 g of 1-cyclohexyl-5-methylhex-5-en-2-one (95% GC, 60% yield).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. concentrationAfter concentration the crude product

Sources & evidence

ORD record
ord-97f40cef822041bd9baf646bd79ca5e1
Source dataset
uspto-grants-2014_09
Patent number
US08841488B2

Linked notes

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