Potassium Hydroxide → 2-(Benzyloxy)-5-hydroxybenzoic acid

HRID 1623661Notes

Reaction equation

HRID 1623661 reaction equation
CC1C=CC(S([O:11][C:12]2[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:16]([CH:21]=2)[C:17]([O:19]C)=[O:18])(=O)=O)=CC=1.[OH-].[K+]>C(O)C.O>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([CH:21]=1)[C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86762539Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate

Product 1

HCID 247719442-(Benzyloxy)-5-hydroxybenzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 75; 9.0 g, 21.82 mmol) was boiled with potassium hydroxide (8.57 g, 153 mmol) in a mixture of ethanol (160 ml) and water (40 ml) for 3 h. After the ethanol had been evaporated, the aqueous solution was washed with ethyl acetate (250 ml), and then acidified with concentrated HCl. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over Na2SO4, and evaporated in vacuo to yield the title compound as a yellow oil. 5.2 g.

Workup

  1. customAfter the ethanol had been evaporated
  2. washthe aqueous solution was washed with ethyl acetate (250 ml)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-256b049ce08e4f8196a6b49e8835c77f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…