Phenol → HCID 12472531, compound

HRID 1389235Notes

Reaction equation

HRID 1389235 reaction equation
[Na].[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.Cl.Cl[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1>CO.C(OCC)C>[O:8]([CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 5360545Sodium

Product 1

HCID 12472531HCID 12472531, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3.5 g (0.15 mole) of sodium in 100 ml of methanol are added 14.1 g (0.15 mole) of phenol. The reaction mixture is evaporated, mixed with 50 ml of N,N-dimethyl formamide and 8.2 g (0.05 mole) of 4-chloromethylpyridine hydrochloride and the reaction mixture heated for 20 hours at 100° C. After cooling, the reaction mixture is mixed with diethyl ether, washed with a dilute aqueous solution of sodium hydroxide and with water, dried over anhydrous sodium sulfate, evaporated and the residue distilled in a vacuum. There are obtained 8.2 g of 4-phenoxymethylpyridine (88% of theory); b.p. 115°-117° C./0.1 mm Hg.

Workup

  1. customThe reaction mixture is evaporated
  2. temperatureAfter cooling
  3. washwashed with a dilute aqueous solution of sodium hydroxide and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. distillationthe residue distilled in a vacuum

Sources & evidence

ORD record
ord-086f9b0c7e7a4dd3a65295d6c6122c01
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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