Ethyl Acetate → 3-Chloro-5-hydroxybenzonitrile

HRID 1874776Notes

Reaction equation

HRID 1874776 reaction equation
[Li+].[Cl-].[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12]C)[CH:11]=1)[C:7]#[N:8].CCOC(C)=O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 219499213-Chloro-5-methoxybenzonitrile

Product 1

HCID 219498783-Chloro-5-hydroxybenzonitrileYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a stirred solution of LiCl (84 g, 1980 mmol) in DMF (500 mL) was added 3-chloro-5-(methyloxy)benzonitrile (167 g, 1000 mmol). The reaction mixture was heated to 180° C. for 12 h. The reaction mixture was poured into ice (300 g) and EtOAc was added. The organic layer was separated, dried over MgSO4 and evaporated to dryness. The solid was recrystallized from EtOAc and petroleum ether (1:5) to afford the title compound (130 g, 67%) as a solid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe solid was recrystallized from EtOAc and petroleum ether (1:5)

Sources & evidence

ORD record
ord-2a62b91b727145e599f9247d2683759e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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