Phenol → Phenyl nicotinate

HRID 633776Notes

Reaction equation

HRID 633776 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.N1C=CC=CC=1>O1CCCC1>[C:1]([O:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 1049PyridineHCID 8471TriethylamineHCID 82604Nicotinoyl chloride

Product 1

HCID 77018Phenyl nicotinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Nicotinic chloride (1.78 g, 10 mmoL) was added to phenol (1.29 g, 12 mmoL) in 10 mL of tetrahydrofuran (THF). Triethylamine (5 mL) and pyridine (5 mL) were then added to the mixture, which was then stirred at room temperature overnight. After THF was evaporated, the mixture was washed with ethyl acetate in water for three times. The ethyl acetate (EtOAC) layer was then purified with silica column (Hexane: EtOAC=4:1) to give pure product. 1H NMR (400 MHz, CDCl3): δ=9.40 (s, 1H), 8.86 (d, 1H), 8.46 (d, 1H), 7.45 (m, 3H), 7.32 (d, 1H), 7.24 (m, 2H).

Workup

  1. customAfter THF was evaporated
  2. washthe mixture was washed with ethyl acetate in water for three times
  3. customThe ethyl acetate (EtOAC) layer was then purified with silica column (Hexane: EtOAC=4:1)
  4. customto give pure product

Sources & evidence

ORD record
ord-9265f1ae3eaa42f38f4dd493ee9f13f2
Source dataset
uspto-grants-2016_04
Patent number
US09321797B2

Reaction notes

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