Methanol → HCID 178495619, compound

HRID 1262481Notes

Reaction equation

HRID 1262481 reaction equation
[Na].[CH3:2][OH:3].C[O-].[Na+].O.[C:8]1([CH3:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH3:2][O:3][CH2:14][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 1140TolueneHCID 5360545Sodium2×HCID 10942334Sodium Methoxide

Product 1

HCID 178495619HCID 178495619, compound

Procedure

Slices of metal sodium (17.4 g, 0.755 mol) were added in small portions to methyl alcohol (250 ml) agitated at room temperature, to prepare sodium methoxide. After metal sodium pieces disappeared, a solution obtained by dissolving compound (C) (200.0 g, 0.581 mol) previously obtained, in dry toluene (600 ml) was gradually added through a dropping funnel so that the inner temperature was kept in the range of 50°~60° C. After the dropwise addition, the mixture was refluxed for 4 hours and then cooled, followed by adding water (20 ml), transfering the mixture into a separating funnel, washing separated toluene layer with water till the aqueous layer became neutral, distilling off toluene under reduced pressure, distilling the residuce under reduced pressure, and collecting a fraction having a boiling point of 105°~108° C./1.5 mmHg to obtain trans-4-methyloxymethyl-1-phenylcyclohexane (D) (100.0 g).

Workup

  1. customa solution obtained
  2. additionwas gradually added through a dropping funnel so that the inner temperature
  3. customwas kept in the range of 50°~60° C
  4. additionAfter the dropwise addition
  5. temperaturethe mixture was refluxed for 4 hours
  6. temperaturecooled
  7. washwashing
  8. customseparated toluene layer with water till the aqueous layer
  9. distillationdistilling off toluene under reduced pressure
  10. distillationdistilling the residuce under reduced pressure
  11. customcollecting a fraction

Sources & evidence

ORD record
ord-f09aa94368124265bddd6bc73d1b5cc8
Source dataset
uspto-grants-1984_06
Patent number
US04452719

Reaction notes

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