Potassium Iodide → HCID 22625362, compound

HRID 2108926Notes

Reaction equation

HRID 2108926 reaction equation
C[C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[CH:5][C:3]=1[OH:4].C([O-])([O-])=O.[K+].[K+].[I-].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:10][C:7]1[CH:6]=[CH:5][C:3]([OH:4])=[CH:2][C:8]=1[CH3:9])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 22625362HCID 22625362, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2,3-dimethylhydroquinone (1.38 g, 10 mmol), K2CO3 (2.76 g, 20 mmol), potassium iodide (0.83 g, 5 mmol) in 50 mL dry acetone was added benzyl bromide (1.88 g, 11 mmol). The resulting suspension was vigorously stirred for 48 at RT. The solid was filtered off and the liquid was concentrated. The residue was chromatographed to afford the benzyl derivative, 4-benzyloxy-3-methyl-phenol, as a light brown solid (1.15 g). 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.49-7.35 (m, 5H), 6.70 (d, J=8.7, 1H), 6.61 (d, J=8.7, 1H), 5.03 (s, 2H), 4.43 (s, 1H), 2.26 (s, 3H), 2.22 (s, 3H); MS (ESI) m/z: 229 (M+H+, 100%).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe liquid was concentrated
  3. customThe residue was chromatographed

Sources & evidence

ORD record
ord-fb39adb10a304bc6868b99f6bd39f5c5
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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