Lithium hydroxide, monohydrate → 3-Benzylbenzoic acid

HRID 1777515Notes

Reaction equation

HRID 1777515 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 597640Methyl 3-benzylbenzoate

Product 1

HCID 41245533-Benzylbenzoic acidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-benzylbenzoate (0.610 g; 2.70 mmol) in THF (14 mL) was added a solution of lithium hydroxide hydrate (0.403 g; 5.39 mmol) in water (12 mL). The mixture was refluxed for 2 hours and concentrated under reduced pressure to remove the THF. The aqueous solution was acidified with 6N hydrochloric acid. The white precipitate formed was collected by filtration, washed with water and dried to afford 0.527 g (92%) of 3-benzylbenzoic acid which was directly used in the next step.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. customto remove the THF
  4. customThe white precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0e8442d540c6478999e9ce430e21a606
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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