Hydrochloric Acid → HCID 688117, compound

HRID 376060Notes

Reaction equation

HRID 376060 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 a 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) are 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) are 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-c289ff8077b54e2abe75700ca7e7e8e7
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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