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

HRID 1623662Notes

Reaction equation

HRID 1623662 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; 22.0 g, 53.3 mmol) was boiled with potassium hydroxide (20.95 g, 373 mmol) in a mixture of ethanol (320 ml) and water (80 ml) overnight. After the ethanol had been evaporated, the aqueous solution was washed with ethyl acetate (500 ml), and then acidified with concentrated HCl. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over sodium sulfate, and evaporated in vacuo to yield the title compound as a yellow oil. 14 g.

Workup

  1. customAfter the ethanol had been evaporated
  2. washthe aqueous solution was washed with ethyl acetate (500 ml)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8be47d2d3bb046f5837edaf2085042dc
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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