Sodium Chloride → cis-4-(4-Hydroxy-3-methoxy-cinnamoyloxy)-1-methyl-1-cyclohexanecarboxylic acid

HRID 2225479Notes

Reaction equation

HRID 2225479 reaction equation
C([O-])=O.[NH4+].[OH:5][C:6]1[CH:29]=[CH:28][C:9](/[CH:10]=[CH:11]\[C:12]([O:14][CH:15]2[CH2:20][CH2:19][C:18]([CH3:27])([C:21]([O:23]CC=C)=[O:22])[CH2:17][CH2:16]2)=[O:13])=[CH:8][C:7]=1[O:30][CH3:31].[Cl-].[Na+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:5][C:6]1[CH:29]=[CH:28][C:9](/[CH:10]=[CH:11]\[C:12]([O:14][CH:15]2[CH2:20][CH2:19][C:18]([CH3:27])([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]2)=[O:13])=[CH:8][C:7]=1[O:30][CH3:31]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 2723923Ammonium formateHCID 67757825Allyl cis-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate

Product 1

HCID 67757505cis-4-(4-Hydroxy-3-methoxy-cinnamoyloxy)-1-methyl-1-cyclohexanecarboxylic acidYield 14.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.2 g of bis(triphenylphosphine)palladium dichloride and 4 g of ammonium formate were added to a solution of 6.2 g of allyl cis-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate (Example 10) in 80 ml of THF. The solution was reacted for 20 hours under an argon stream, while it was refluxed. After reaction, 150 ml of an aqueous sodium chloride solution was added to the reaction solution. The solution was extracted three times with 70 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and dried over magnesium sulfate. Then, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=1:2, the solvent was removed in vacuo, yielding 0.8 g of cis-4-(4-hydroxy-3-methoxy-cinnamoyloxy)-1-methyl-1-cyclohexanecarboxylic acid (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 20 hours under an argon stream
  2. temperaturewhile it was refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 70 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed three times with an aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThen, the solvent was removed in vacuo
  9. customThe oily substance obtained
  10. washFrom the fraction eluted with hexane and ethyl acetate=1:2
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3efb9b63656341e9b835057a1d2e94c7
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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