Sodium Chloride → 3-Hydroxy-4-methoxybenzonitrile

HRID 646537Notes

Reaction equation

HRID 646537 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C([O-])=O.[Na+].S(O)(O)(=O)=O.[NH2:21]O.[Cl-].[Na+]>O.C(O)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:21]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 12127IsovanillinHCID 159255Hydroxylamine, sulfate (1:1)HCID 2723810Sodium Formate

Product 1

HCID 49128223-Hydroxy-4-methoxybenzonitrileYield 138.4%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

3-Hydroxy-4-methoxybenzaldehyde (36.7 kg) and sodium formate (30.6 kg) were added to formic acid (96%, 204 kg) and the resultant mixture was heated to approximately 85° C. Hydroxylamine sulphate (21.6 kg) was added in eight equal portions at 30 minute intervals and the mixture was heated to 85° C. for 5 hours. The resultant mixture was cooled to approximately 25° C. and added to a solution of sodium chloride (140 kg) in water (700 liters). The resultant solid was collected by filtration, washed with water and dried to give 3-hydroxy-4-methoxybenzonitrile (34 kg, 94%; Chemical Abstracts Registry Number 5280546-6).

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-33e0138d5af4488dad7e3a63de486704
Source dataset
uspto-grants-2010_04
Patent number
US07705145B2

Reaction notes

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