Phenol → HCID 14937588, compound

HRID 593385Notes

Reaction equation

HRID 593385 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[O:19].[Cl-].[NH4+]>ClCCl>[OH:19][CH:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[OH:11]

Participants

6

Reactant 4

HCID 996PhenolHCID 142732-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14937588HCID 14937588, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of AlCl3 (1.42 g) in dichloromethane (20 mL) at 0° C. is added a solution of phenol (1 g) in dichloromethane (20 mL) and the mixture is stirred at this temperature for 40 minutes. After addition of a solution of pyridine-2-carboxaldehyde (1.21 g) in dichloromethane (10 mL), the mixture is allowed to warm at room temperature for 4 hours, then cooled to 0° C., treated dropwise with aqueous ammonium chloride and stirred at room temperature for 30 minutes. The aqueous phase is extracted twice with dichloromethane and pooled organic extracts dried over magnesium sulfate and concentrated. The residue is purified by column chromatography over silica gel (gradient heptane/ethyl acetate from 100/0 to 70/30) to afford pure 2-(hydroxy-pyridin-2-yl-methyl)-phenol.

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred at room temperature for 30 minutes
  3. extractionThe aqueous phase is extracted twice with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography over silica gel (gradient heptane/ethyl acetate from 100/0 to 70/30)

Sources & evidence

ORD record
ord-a153247dff444ec79609ab5328984205
Source dataset
uspto-grants-2016_01
Patent number
US09242959B2

Reaction notes

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