Benzyl Bromide → HCID 67107653, compound

HRID 1623618Notes

Reaction equation

HRID 1623618 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH3:18][CH: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][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:11])[CH3:19]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 125400492-Hydroxy-5-(propan-2-yl)benzoic acid

Product 1

HCID 67107653HCID 67107653, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (3.83 g, 27.7 mmol) was added to a stirred solution of 2-hydroxy-5-(1-methylethyl)benzoic acid (may be prepared as described in Description 1; 2.0 g, 11.10 mmol) in acetone (80 ml), followed by the addition of (bromomethyl)benzene (4.75 g, 27.7 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, using 1:10 ethyl acetate-petroleum ether yielded the title compound as a yellow oil. 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

Sources & evidence

ORD record
ord-453fa028f95d48599d3350506ff238e4
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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