2-Hydroxy-p-toluic acid → HCID 14519881, compound

HRID 1198624Notes

Reaction equation

HRID 1198624 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[OH-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 57882-Hydroxy-p-toluic acidHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide

Product 1

HCID 14519881HCID 14519881, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A two-phase mixture of 45.6 g (0.3 mol) 4-methylsalicylic acid, NaOH (36 g, 0.9 mol), benzyl bromide (154 g, 0.9 mol) and tetrabutylammonium bromide (10 g, 30 mmol) in water (200 ml) and CH2Cl2 (200 ml) was stirred at room temperature for 3 hours. The layers were separated and the CH2Cl2 was removed from the organic fraction. The residue was dissolved in a mixture of ethanol (250 ml) and 2N NaOH (50 ml), and the mixture was heated under reflux for 30 min. The ethanol was removed under vacuum and the residue was diluted with water and washed with ethyl acetate. The aqueous layer was separated and acidified with dilute HCl to give a precipitate of 4-methyl-2-phenylmethoxybenzoic acid (65.3 g, 90%) m.p. (MeOH aq) 105°-107° C. Anal (C15H14O3) C,H,O.

Workup

  1. customThe layers were separated
  2. customthe CH2Cl2 was removed from the organic fraction
  3. dissolutionThe residue was dissolved in a mixture of ethanol (250 ml) and 2N NaOH (50 ml)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 30 min
  6. customThe ethanol was removed under vacuum
  7. additionthe residue was diluted with water
  8. washwashed with ethyl acetate
  9. customThe aqueous layer was separated

Sources & evidence

ORD record
ord-051ded77ca494c35a0cf1e703438cc06
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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