Methanol → 2-Chloro-3-(1-cyanocyclopropyl)benzoic acid

HRID 2190455Notes

Reaction equation

HRID 2190455 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O1CCCC1.CO>O>[Cl:1][C:2]1[C:11]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 67311674Methyl 2-chloro-3-(1-cyanocyclopropyl)benzoate

Product 1

HCID 668103062-Chloro-3-(1-cyanocyclopropyl)benzoic acidYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using methyl 2-chloro-3-(1-cyanocyclopropyl)benzoate (684 mg, 2.90 mmol), lithium hydroxide•monohydrate (207 mg, 4.93 mmol), tetrahydrofuran (10 mL), methanol (3 mL) and water (3 mL) as starting materials, and in the same manner as in Example A1(iii), the title compound (457 mg, 71%) was obtained as a white powder.

Sources & evidence

ORD record
ord-b0f04afce995453b9ab0e5406199eecb
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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