Benzyl Bromide → HCID 21544507, compound

HRID 1623628Notes

Reaction equation

HRID 1623628 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH3:18][O: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][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:11]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 757875-Methoxysalicylic Acid

Product 1

HCID 21544507HCID 21544507, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (690 mg, 5.00 mmol) was added to a stirred solution of 2-hydroxy-5-(methyloxy)benzoic acid (336 mg, 2.00 mmol) in acetone (20 ml) followed by the addition of ((bromomethyl)benzene (854 mg, 5.00 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. Flash chromatography over silica gel eluting with 1:10 ethyl acetate:petroleum ether yielded the title compound as a pure, white powder. 500 mg.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to a yellow solid

Sources & evidence

ORD record
ord-64acd23db5e048608f9a919c4351668f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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