3-Chlorophenol → 2-(3-Chlorophenoxy)nicotinic acid

HRID 1413651Notes

Reaction equation

HRID 1413651 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C[O-].[Na+]>CO>[Cl:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 762582-Chloronicotinic acidHCID 10942334Sodium Methoxide

Product 1

HCID 122026412-(3-Chlorophenoxy)nicotinic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the same manner as in Example 1(a), 15.8 grams (0.1 mole) 2-chloronicotinic acid, 64.0 grams (0.5 mole) 3-chlorophenol, 45 grams (0.21 mole) 25% sodium methoxide solution and 100 milliliters methanol were combined to produce 22.1 grams (88.6% of theoretical yield) of 2-(3-chlorophenoxy) nicotinic acid, m.p. 161°-164° C.

Sources & evidence

ORD record
ord-a9a53cb06af14ca8bf57205d98505995
Source dataset
uspto-grants-1981_02
Patent number
US04251263

Reaction notes

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