Sodium Hydroxide → HCID 580726, compound

HRID 485153Notes

Reaction equation

HRID 485153 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH2:14][CH2:15][CH3:16])=[C:9]([O:11][CH3:12])[CH:10]=1)(=O)C.[OH-].[Na+]>CO>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([OH:4])[CH:6]=[CH:7][C:8]=1[O:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20271553HCID 20271553, compound

Product 1

HCID 580726HCID 580726, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Acetoxy-2-n-propoxyanisole (39.9 g, 0.178 M), 1.67 N sodium hydroxide solution (300 ml) and methanol (300 ml) were refluxed with stirring (1 hr). The methanol was then removed, the residue diluted with water and extracted with ether. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with ether. The combined extracts were washed with water, dried (sodium sulphate) and evaporated. The product was then passed through a short pad of florisil eluting with chloroform-methanol (95:5) and the filtrate evaporated to give 3-methoxy-4-n-propoxyphenol as an oil which solidified on standing. After trituration with 40/60 petrol and filtration the product had m.p. 54°-56° C.

Workup

  1. customThe methanol was then removed
  2. additionthe residue diluted with water
  3. extractionextracted with ether
  4. extractionextracted with ether
  5. washThe combined extracts were washed with water
  6. dry with materialdried (sodium sulphate)
  7. customevaporated
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e5f371b416de440ea9bc08f5b6fb823b
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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