Methanol → HCID 13463451, compound

HRID 1656812Notes

Reaction equation

HRID 1656812 reaction equation
[Na].CO.C[O-].[Na+:6].[OH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:8][O-:7].[Na+:6].[CH3:12][CH:11]([CH2:16][CH3:17])[CH2:10][CH2:9][CH2:8][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7456MethylparabenHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 2

HCID 10942334Sodium MethoxideHCID 13463451HCID 13463451, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Conditions

Temperature
25 °C

Procedure

Sodium methylate was prepared by reacting sodium (2.3 g, 0.1 mol) with 100 ml anhydrous methanol. To the sodium methylate was added methyl 4-hydroxybenzoate (15.2 g, 0.1 mol). Excess methanol was removed under reduced pressure and toluene was added and removed under reduced pressure to remove any residual methanol. The solid residue was dissolved in 2:1 toluene-dimethylformamide and S-4-methylhexyl bromide (17.9 g, 0.1 mol) was added as a single portion and the mixture was refluxed for 1 day. The reaction product was cooled and washed 3 times with 100 ml water. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. This crude methyl S-4-(4-methylhexyloxy)benzoate was refluxed in 100 ml of 10% aqueous sodium hydroxide for 1 day. The reaction product was cooled to room temperature (25° C.) and acidified with concentrated aqueous HCl. The precipated solid was collected by filtration and washed several times with cool water. This material was purified by recrystallization from ethanol-water. S- 4-(4-Methylhexyloxy)benzoic acid (20 g, 85% yield) was obtained. NMR and MS were consistent for the product.

Workup

  1. customExcess methanol was removed under reduced pressure and toluene
  2. additionwas added
  3. customremoved under reduced pressure
  4. customto remove any residual methanol
  5. additionwas added as a single portion
  6. temperaturethe mixture was refluxed for 1 day
  7. temperatureThe reaction product was cooled
  8. washwashed 3 times with 100 ml water
  9. dry with materialThe organic layer was dried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. temperatureThis crude methyl S-4-(4-methylhexyloxy)benzoate was refluxed in 100 ml of 10% aqueous sodium hydroxide for 1 day
  13. filtrationThe precipated solid was collected by filtration
  14. washwashed several times with cool water
  15. customThis material was purified by recrystallization from ethanol-water

Sources & evidence

ORD record
ord-9211be8f4eb14970abf1612371f826f4
Source dataset
uspto-grants-1993_10
Patent number
US05254747

Reaction notes

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