Sodium Chloride → Allyl 4-(4-hydroxy3-methoxycinnamoyl)-1-methyl-1-cyclohexanecarboxylate

HRID 2225496Notes

Reaction equation

HRID 2225496 reaction equation
Cl.CO.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:26]=[CH:27][C:28]=1[O:29]C1CCCCO1)[CH:9]=[CH:10][C:11]([CH:13]1[CH2:18][CH2:17][C:16]([CH3:25])([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH2:15][CH2:14]1)=[O:12].[Cl-].[Na+]>CO>[OH:29][C:28]1[CH:27]=[CH:26][C:8]([CH:9]=[CH:10][C:11]([CH:13]2[CH2:14][CH2:15][C:16]([CH3:25])([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH2:17][CH2:18]2)=[O:12])=[CH:7][C:6]=1[O:5][CH3:4]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 21893726Hydrochloride methanolHCID 67758353Allyl 4-[3-methoxy-4-(2-tetrahydropyranyloxy)cinnamoyl]-1-methyl-1-cyclohexanecarboxylate

Product 1

HCID 54322730Allyl 4-(4-hydroxy3-methoxycinnamoyl)-1-methyl-1-cyclohexanecarboxylateYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 ml of 2N hydrochloric acid - methanol was added to a solution of 1.1 g of allyl 4-[3-methoxy-4-(2-tetrahydropyranyloxy)cinnamoyl]-1-methyl-1-cyclohexanecarboxylate (Example 38) in 30 ml of methanol. The solution was stirred for 0.5 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 50 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 0.85 g of allyl 4-(4-hydroxy3-methoxycinnamoyl)-1-methyl-1-cyclohexanecarboxylate (a compound of the present invention) as a pale yellow oil, 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 twice with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThereafter, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-922eba9c5f6f4ce2bbf7b5b3bc215f62
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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