5-Methylsalicylic acid → Phenylmethyl 5-methyl-2-[(phenylmethyl)oxy]benzoate

HRID 1623630Notes

Reaction equation

HRID 1623630 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH3:17][C:14]1[CH:15]=[CH:16][C:8]([O:7][CH2:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:8]=2)=[C:9]([CH:13]=1)[C:10]([O:12][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:11]

Participants

5

Reactant 3

HCID 69735-Methylsalicylic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 67106895Phenylmethyl 5-methyl-2-[(phenylmethyl)oxy]benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (1379 mg, 9.99 mmol) was added to a stirred solution of 2-hydroxy-5-methylbenzoic acid (608 mg, 4.00 mmol) in acetone (10 ml), followed by the addition of (bromomethyl)benzene (1709 mg, 9.99 mmol). The mixture was refluxed for 12 h and then cooled to room temperature. The mixture was filtered and the filtrate was concentrated to a yellow solid. The crude product was purified by Flash chromatography over silica gel, eluting with 1:10 ethyl acetate-petroleum ether to yield the title compound as a white powder. 1.0 g.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to a yellow solid
  4. customThe crude product was purified by Flash chromatography over silica gel
  5. washeluting with 1:10 ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-f18d17577d814b0daaf75012181c1517
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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