Hydrochloric Acid → 4-[hydroxy(phenyl)methyl]benzoic acid

HRID 1180376Notes

Reaction equation

HRID 1180376 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1.CO.[OH-].[K+].Cl>C1COCC1>[OH:1][CH:2]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 11776502HCID 11776502, compound

Product 1

HCID 2363614-[hydroxy(phenyl)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-[hydroxy(phenyl)methyl]benzoate from step 1 (1.6 g, 6.6 mmol) in THF (40 mL) was added methanol (13 mL) and 1.0N aqueous potassium hydroxide solution (13.2 mL, 13.2 mmol). The mixture was heated at 70° C. for 20 minutes and then cooled down to room temperature. Methanol and THF were evaporated under reduced pressure. 3.0N hydrochloric acid (7.5 mL, 22.5 mmol) was added to the crude residue. The solid obtained was filtered to afford the title acid as a white solid. The resulting crude compound was used as such in the next step.

Workup

  1. temperaturecooled down to room temperature
  2. customMethanol and THF were evaporated under reduced pressure
  3. customThe solid obtained
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-ab97ebf0c9af4e6891eb1ce4ef3641dd
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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