Methanol → HCID 178495619, compound

HRID 1248096Notes

Reaction equation

HRID 1248096 reaction equation
[CH3:1][OH:2].C[O-].[Na+].O.[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH3:1][O:2][CH2:13][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:9][CH2:8]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1140TolueneHCID 10942334Sodium Methoxide

Product 1

HCID 178495619HCID 178495619, compound

Procedure

Slices of metal Na (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 Na pieces disappeared, a solution obtained by dissolving the compound (IV) (200.0 g, 0.581 mol) obtained above, in dry toluene (600 ml), was gradually added through a dropping funnel so that the inner temperature could keep within a range of 50° to 60° C. After completion of the addition, the mixture was refluxed for 4 hours, followed by cooling, adding water (20 ml), transferring into a separating funnel, washing the resulting toluene layer with water until the aqueous layer became neutral, distilling off toluene under reduced pressure, distilling under reduced pressure and collecting fractions of boiling points of 105°~108° C./1.5 mmHg to obtain trans-4-methyloxymethyl-1-phenylcyclohexane (V) (100.0 g).

Workup

  1. customa solution obtained
  2. additionwas gradually added through a dropping funnel so that the inner temperature
  3. customcould keep within a range of 50° to 60° C
  4. additionAfter completion of the addition
  5. temperaturethe mixture was refluxed for 4 hours
  6. temperatureby cooling
  7. customtransferring into a separating funnel
  8. washwashing the resulting toluene layer with water until the aqueous layer
  9. distillationdistilling off toluene under reduced pressure
  10. distillationdistilling under reduced pressure
  11. customcollecting fractions of boiling points of 105°~108° C./1.5 mmHg

Sources & evidence

ORD record
ord-82be00538eae4d1f9d5f79e66fcce23c
Source dataset
uspto-grants-1985_06
Patent number
US04522741

Reaction notes

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