Potassium Iodide → HCID 22625362, compound

HRID 1666737Notes

Reaction equation

HRID 1666737 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-df37be21f3054394bba7165e01a6080b
Source dataset
uspto-grants-2011_10
Patent number
US08044097B2

Reaction notes

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