Sodium Chloride → HCID 19004629, compound

HRID 2225494Notes

Reaction equation

HRID 2225494 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][C:7]([CH3:13])([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22].[Cl-].[Na+]>CN(C=O)C>[C:1]([CH:4]1[CH2:9][CH2:8][C:7]([CH3:13])([C:10]([O:12][CH2:22][CH:21]=[CH2:20])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 190047484-Acetyl-1-methyl-1-cyclohexanecarboxylic acid

Product 1

HCID 19004629HCID 19004629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.4 g of 4-acetyl-1-methyl-1-cyclohexanecarboxylic acid (Example 36) was dissolved in 50 ml of DMF, and 5 g of potassium carbonate and 3 ml of allyl bromide were added to the resultant solution. The solution was reacted for 6 hours at room temperature. After reaction, 100 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 30 ml of methylene chloride. The organic layer obtained was washed three times with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 20 g of silica gel. From the fraction eluted with hexane and ethyl acetate=10:1, the solvent was removed in vacuo, yielding obtaining 1.5 g of allyl 4-acetyl-1-methyl-1-cyclohexanecarboxylate as a colorless oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 6 hours at room temperature
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 30 ml of methylene chloride
  4. customThe organic layer obtained
  5. washwas washed three times with an aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo
  8. customThe oily substance obtained
  9. washFrom the fraction eluted with hexane and ethyl acetate=10:1
  10. customthe solvent was removed in vacuo
  11. customyielding

Sources & evidence

ORD record
ord-144d4015ffca4652b66794f0b097e054
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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