Pyridine → Allyl cis-4-(4-acetoxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate

HRID 2225477

Reaction equation

HRID 2225477 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](Cl)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].C([C@H:21]1[CH2:26][C@@H:25]([OH:27])[CH2:24][CH2:23][C:22]1([CH3:31])[C:28]([OH:30])=[O:29])C=C.N1C=C[CH:35]=[CH:34][CH:33]=1>>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8](/[CH:9]=[CH:10]\[C:11]([O:27][CH:25]2[CH2:26][CH2:21][C:22]([CH3:31])([C:28]([O:30][CH2:35][CH:34]=[CH2:33])=[O:29])[CH2:23][CH2:24]2)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 544680224-Acetoxy-3-methoxycinnamoyl chlorideHCID 67842177Allyl cis-4-hydroxy-1-methyl-1-cyclohexanecarboxylic acid

Product 1

HCID 67757065Allyl cis-4-(4-acetoxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate

Procedure

2.3 g of 4-acetoxy-3-methoxycinnamoyl chloride, disclosed in the literature [K. Freudenberg and R. Dillenburg, Chem. Ber., 84, 67-70 (1951), was added to a solution of 1.8 g of allyl cis-4-hydroxy-1-methyl-1-cyclohexanecarboxylic acid (Example 7) in 70 ml of pyridine. The resultant solution was reacted at room temperature for 18 hours. After reaction, the solvent was removed in vacuo. To the residue, 150 ml of 2N hydrochloric acid was added. The resultant solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with 2N hydrochloric acid, once with an aqueous sodium hydrogencarbonate solution and once with an aqueous sodium chloride solution, and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The resultant oily substance was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 1.6 g of allyl cis-4--(4-acetoxy-3-methoxycinnamoyloxy)-1-methyl-1-cyclohexanecarboxylate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customAfter reaction
  2. customthe solvent was removed in vacuo
  3. additionTo the residue, 150 ml of 2N hydrochloric acid was added
  4. extractionThe resultant solution was extracted three times with 50 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed three times with 2N hydrochloric acid
  7. dry with materialonce with an aqueous sodium hydrogencarbonate solution and once with an aqueous sodium chloride solution, and dried over magnesium sulfate
  8. customThereafter, the solvent was removed in vacuo
  9. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2024d67d452d48878660a492f5d87bea
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Linked notes

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