Hydrochloric Acid → 2-(Benzyloxy)-5-methylbenzoic acid

HRID 614822

Reaction equation

HRID 614822 reaction equation
[CH3:1][C:2]1[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>S1(CCCC1)(=O)=O.O>[CH2:13]([O:12][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 89802Methyl 5-methylsalicylate2×

Product 1

HCID 130269142-(Benzyloxy)-5-methylbenzoic acidYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 31347SulfolaneSolvent

Procedure

5-Methylsalicylic acid was reacted with methanol and sulphuric acid by the general method of Brunner (Monatsh. 1913, 34, 916) to give methyl 5-methylsalicylate, b.p. 115°-116° C./10 mmHg. This ester (12.0 g) was heated together with benzyl chloride (9.1 g) and anhydrous potassium carbonate (5.0 g) in dry sulpholane (90 ml) at 100° C. for 22 hours. The mixture was then poured into a mixture of ice and water (1200 ml) to give crude methyl 2-benzyloxy-5-methylbenzoate (17.6 g). This ester (4.3 g) was heated at reflux with aqueous sodium hydroxide solution (2N; 100 ml) for 2 hours and the mixture was then cooled, diluted with water, and acidified to pH 2 by treatment with concentrated hydrochloric acid to give 2-benzyloxy-5-methylbenzoic acid (3.65 g), m.p. 98°-100° C.

Workup

  1. customto give crude methyl 2-benzyloxy-5-methylbenzoate (17.6 g)
  2. temperaturethe mixture was then cooled

Sources & evidence

ORD record
ord-680aa1b6955d41f082c43e5f16bfbef3
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Linked notes

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