Sulfuric Acid → HCID 178443559, compound

HRID 650848Notes

Reaction equation

HRID 650848 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15][C:16]2[CH:27]=[CH:26][C:19]([CH:20]=[CH:21][C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(=O)(=O)(O)O>[OH-].[K+]>[CH2:1]([C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH:20]=[CH:21][C:22]([OH:24])=[O:23])=[CH:26][CH:27]=2)[CH2:12][CH2:13]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178443560HCID 178443560, compound

Product 1

HCID 178443559HCID 178443559, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 8 g of methyl 4-[(trans-4-heptylcyclohexyl)methoxy]cinnamate and 50 ml of 10 percent methanolic potassium hydroxide solution is allowed to stand for 16 hours at room temperature. Thereafter, acidification is effected with aqueous 1 N sulfuric acid with continuous stirring and with cooling, extraction is effected with methylene chloride and the organic phase is washed several times with water, dried over magnesium sulfate and evaporated down. Crystallization from hexane/ethyl acetate gives 4-[(trans-4-heptylcyclohexyl)methoxy]cinnamic acid.

Workup

  1. temperaturewith cooling
  2. extractionextraction
  3. washthe organic phase is washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. customCrystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-300330a532a1449a8dc81aa9f6e2365d
Source dataset
uspto-grants-2001_08
Patent number
US06277502B1

Reaction notes

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