Hydrochloric Acid → HCID 688117, compound

HRID 6071Notes

Reaction equation

HRID 6071 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[CH2:11]([OH:13])[CH3:12]>ClCCl>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[NH:7])[O:13][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 130194-Cyanophenol

Product 1

HCID 688117HCID 688117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, 0° C. solution of 4-hydroxybenzonitrile (50.7 g, 426 mmol) in 1400 mL of dichloromethane and 75 mL anhydrous ethanol is treated with anhydrous hydrogen chloride gas (110 g) over 1.5 hours. This solution is stirred at room temperature for 64 hours and the resulting solids collected and washed with 500 mL diethyl ether and 2×1000 mL of ethyl acetate. The remaining solids (60.4 g) were dissolved in 1200 mL of water and the residual solids filtered. To the filtrate is added a solution of sodium hydroxide (12.57 g) in 150 mL water. The resulting white solid is filtered and washed with water to afford ethyl 4-hydroxybenzenecarboximidoate.

Workup

  1. customthe resulting solids collected
  2. washwashed with 500 mL diethyl ether and 2×1000 mL of ethyl acetate
  3. dissolutionThe remaining solids (60.4 g) were dissolved in 1200 mL of water
  4. filtrationthe residual solids filtered
  5. additionTo the filtrate is added a solution of sodium hydroxide (12.57 g) in 150 mL water
  6. filtrationThe resulting white solid is filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-185e1d513d024f29aeed40745a08febf
Source dataset
uspto-grants-1993_09
Patent number
US05246965

Reaction notes

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