Sodium Hydroxide → 5-(Benzyloxy)-2-methylbenzoic acid

HRID 709686Notes

Reaction equation

HRID 709686 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:25])=[C:13]([CH:24]=1)[C:14]([O:16]CC1C=CC=CC=1)=[O:15])[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]=[CH:11][C:12]([CH3:25])=[C:13]([CH:24]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67363220Benzyl 5-(benzyloxy)-2-methylbenzoate

Product 1

HCID 597600475-(Benzyloxy)-2-methylbenzoic acidYield 83.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 5-(benzyloxy)-2-methylbenzoate (2.80 g) in methanol (50 mL) and THF (50 mL) was added a solution of sodium hydroxide (3.30 g) in water (50 mL), and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture and the mixture was concentrated. Water (30 mL) was added to the residue, and the mixture was adjusted with 2N hydrochloric acid to pH<2. The precipitated crystals were collected by filtration, and dried to give the title compound (1.70 g) as a white solid. This compound was used for the next step without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. additionWater (30 mL) was added to the residue
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-7b03f0fba5e04004b1a93756ff60c782
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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