Sodium Hydroxide → 2-[4-(Oxan-4-yl)phenoxy]propanoic acid

HRID 1678974Notes

Reaction equation

HRID 1678974 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH:12]([CH3:18])[C:13]([O:15]CC)=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH:12]([CH3:18])[C:13]([OH:15])=[O:14])=[CH:19][CH:20]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22765982Ethyl 2-[4-(oxan-4-yl)phenoxy]propanoate

Product 1

HCID 203654662-[4-(Oxan-4-yl)phenoxy]propanoic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.6 g of ethyl 2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoate were added to a solution of 17 ml of 2N sodium hydroxide and 100 ml of ethanol and the mixture was stirred for 2 hours at room temperature and then was refluxed for 30 minutes. The mixture was evaporated to dryness and the residue was dissolved in 20 ml of N sodium hydroxide. The solution was washed with ether and acidified with 4N hydrochloric acid. The mixture was filtered and the recovered crystals were washed with water and dried. The product was crystallized from a 50-50 cyclohexane-ethyl acetate mixture to obtain 6.1 g of 2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoic acid melting at 156° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in 20 ml of N sodium hydroxide
  4. washThe solution was washed with ether
  5. filtrationThe mixture was filtered
  6. washthe recovered crystals were washed with water
  7. customdried
  8. customThe product was crystallized from a 50-50 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-03cd5983ed1f4051a3b5dd1ff1f062f2
Source dataset
uspto-grants-1978_03
Patent number
US04078076

Reaction notes

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