Benzoate → Benzoic Acid

HRID 1035709Notes

Reaction equation

HRID 1035709 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.CO>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 242BenzoateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.150 g ethyl trans-4-[4-(E)-2-tert-butoxycarbonylvinyl)cyclohexyl]benzoate (0.42 mmol, 1 eq.) is dissolved in 3 mL of a 2/1 mixture of THF/methanol. At 0° C., 0.07 g of lithium hydroxide monohydrate (1.67 mmol; 4 eq.) is added with stirring. After 3 hours at room temperature, the reaction medium is evaporated and aqueous 6% sulfur dioxide solution is added. The precipitate is filtered off and washed with water to give 0.085 g of trans-4-[4-(E)-2-tert-butoxycarbonylvinyl)cyclohexyl]benzoic acid.

Workup

  1. customthe reaction medium is evaporated
  2. additionaqueous 6% sulfur dioxide solution is added
  3. filtrationThe precipitate is filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-ccdbc6a0568e4d16912d15319a853b7c
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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