Phenol → Phenyl nicotinate

HRID 1467377Notes

Reaction equation

HRID 1467377 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). 2′,3′,5′-Triacetyl ethyl nicotinate riboside (2):

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-bc246c2011274e0d82c0c116932f0867
Source dataset
uspto-grants-2015_04
Patent number
US09000147B2

Reaction notes

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