Methanol → HCID 178448073, compound

HRID 246811Notes

Reaction equation

HRID 246811 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 toluene 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 toluene 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-dc45523af7e243bcbbae4d74885fa6b7
Source dataset
uspto-grants-1987_11
Patent number
US04704228

Reaction notes

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