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

HRID 1623660Notes

Reaction equation

HRID 1623660 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 37; 2.5 g, 6.06 mmol) was boiled with potassium hydroxide (2.38 g, 42.4 mmol) in a mixture of ethanol (60 ml) and water (15 ml) for 4 h. After the ethanol had been evaporated, the aqueous solution was washed with ethyl acetate (20 ml) and acidified with concentrated HCl. The mixture was extracted with ethyl acetate (3×30 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulphate and evaporated in vacuo to yield the title compound as a yellow oil. 1.35 g.

Workup

  1. customAfter the ethanol had been evaporated
  2. washthe aqueous solution was washed with ethyl acetate (20 ml)
  3. extractionThe mixture was extracted with ethyl acetate (3×30 ml)
  4. washThe organic phase was washed with saturated brine (25 ml)
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-396329d062ac425c8aa7258764818e9a
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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