Hydrochloric Acid → Allyl cis-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate

HRID 2225478Notes

Reaction equation

HRID 2225478 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:34]=[CH:33][C:14](/[CH:15]=[CH:16]\[C:17]([O:19][CH:20]2[CH2:25][CH2:24][C:23]([CH3:32])([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])[CH2:22][CH2:21]2)=[O:18])=[CH:13][C:12]=1[O:35][CH3:36])(=O)C.Cl>CO>[OH:10][C:11]1[CH:34]=[CH:33][C:14](/[CH:15]=[CH:16]\[C:17]([O:19][CH:20]2[CH2:25][CH2:24][C:23]([CH3:32])([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])[CH2:22][CH2:21]2)=[O:18])=[CH:13][C:12]=1[O:35][CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67757065Allyl cis-4-(4-acetoxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate

Product 1

HCID 67757825Allyl cis-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylateYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g of potassium carbonate was added to a solution of 1.6 g of allyl cis-4-(4-acetoxy-3-methoxycinnamoyloxy )-1-methyl-1-cyclohexanecarboxylate (Example 9) in 80 ml of methanol. The resultant solution was stirred for 2 hours at room temperature. After reaction, 2N hydrochloric acid was added to the reaction solution, acidifying the solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed once with an aqueous sodium hydrogencarbonate solution and once with an aqueous sodium chloride solution, and was then dried over magnesium sulfate. The solvent was removed in vacuo, yielding 0.62 g of allyl cis-4--(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1cyclohexanecarboxylate (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. additionwas added to the reaction solution
  2. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  3. customThe organic layer obtained
  4. washwas washed once with an aqueous sodium hydrogencarbonate solution and once with an aqueous sodium chloride solution
  5. dry with materialwas then dried over magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-75832af586114a79a8dc3ad43b589434
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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