Hydrochloric Acid → HCID 19004662, compound

HRID 2225480Notes

Reaction equation

HRID 2225480 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 19004694HCID 19004694, compound

Product 1

HCID 19004662HCID 19004662, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g of potassium carbonate was added to a solution of 1.4 g of allyl trans-4-(4-acetoxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate (Example 12) in 70 ml of methanol. The resultant solution was stirred for 2 hours at room temperature. After reaction, 2N hydrochloric acid was added to the 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 1.09 g of allyl trans-4-(4-hydroxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. additionwas added to the 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-1f2cd500cb474a389a07a1e2cfcc547e
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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