Sodium Hydroxide → 3-(Benzyloxy)-4-methylbenzoic acid

HRID 709657Notes

Reaction equation

HRID 709657 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 584372413-Benzyloxy-4-methylbenzoic acid benzyl ester

Product 1

HCID 229031883-(Benzyloxy)-4-methylbenzoic acidYield 89.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzyl 3-(benzyloxy)-4-methylbenzoate (4.30 g) in methanol (40 mL) and THF (40 mL) was added a solution of sodium hydroxide (2.60 g) in water (40 mL), and the mixture was stirred at 70° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and evaporated under reduced pressure. Water (20 mL) was added to the residue, and the mixture was adjusted with 1N hydrochloric acid to pH<4. The precipitated crystals were collected by filtration, and dried to give the title compound (2.80 g) as white crystals.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated under reduced pressure
  3. additionWater (20 mL) was added to the residue
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-eccaeb3ba55244ea9dc44c688cbddb67
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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