Resorcinol → HCID 22241441, compound

HRID 892133Notes

Reaction equation

HRID 892133 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:12]=1[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=2)[C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoate

Product 1

HCID 22241441HCID 22241441, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-hydroxy-phenol (1.5 g, 13.6 mmol) in acetonitrile (50 mL) is added methyl 2-(bromomethyl)-6-methyl-benzoate (0.82 g, 3.4 mmol, example 2) followed by K2CO3 (3.76 g, 27.2 mmol). The resulting mixture is heated to 50° C. and stirred at this temperature for 90 min. then cooled, filtered and the filtrate concentrated under vacuum. The residue is purified by flash chromatography (silica, 5% ethyl acetate in dichloromethane) to give the title compound as a white solid. MS (EI) 272 (M+).

Workup

  1. temperaturethen cooled
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue is purified by flash chromatography (silica, 5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-857deb19e4c74f95a4dd1d4bd6a568c8
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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