Methanol → HCID 178448073, compound

HRID 2164707Notes

Reaction equation

HRID 2164707 reaction equation
[CH3:1]O.S(=O)(=O)(O)O.[CH2:8]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)[CH2:9][CH3:10].O>C1(C)C=CC=CC=1>[CH3:1][O:24][C:23]([C@H:20]1[CH2:21][CH2:22][C@H:17]([C@H:14]2[CH2:15][CH2:16][C@H:11]([CH2:8][CH2:9][CH3:10])[CH2:12][CH2:13]2)[CH2:18][CH2:19]1)=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 178448072HCID 178448072, compound

Product 1

HCID 178448073HCID 178448073, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl alcohol (200 ml) and conc. sulfuric acid (15 ml) were added to trans-4-(trans-4'-propylcyclohexyl)cyclohexanecarboxylic acid (68.2 g, 0.27 mol) and the mixture was heated under reflux for 4 hours, followed by cooling, adding water (200 ml) and toluene (100 ml), transferring the resulting mixture to a separating funnel, three times washing the foluene layer with water (each time 100 ml), distilling off toluene, adding ethyl alcohol (40 ml) to the residue, recrystallizing, filtering off and drying to obtain the objective trans-4-(trans-4'-propylcyclohexyl)cyclohexanecarboxylic acid methyl ester (65 g) (yield: 90.2%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureby cooling
  4. washthree times washing the foluene layer with water (each time 100 ml),
  5. distillationdistilling off toluene
  6. additionadding ethyl alcohol (40 ml) to the residue
  7. customrecrystallizing
  8. filtrationfiltering off
  9. customdrying

Sources & evidence

ORD record
ord-65b46dffae1f44adaba90db01d3a645e
Source dataset
uspto-grants-1985_03
Patent number
US04507222

Reaction notes

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