Sulfuric Acid → 2,6-Difluorobenzyl alcohol

HRID 1281241Notes

Reaction equation

HRID 1281241 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:8]=1[CH2:9]N.N([O-])=[O:17].[Na+].C(=O)([O-])O.[Na+]>O>[F:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:8]=1[CH2:9][OH:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1235632,6-DifluorobenzylamineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 879212,6-Difluorobenzyl alcoholYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

75 g of 10% aqueous sulfuric acid solution was charged, and 14.3 g of 2,6-difluorobenzylamine obtained in Example 1 was dropwise added thereto under cooling. Then, under cooling, a solution comprising 10.4 g of sodium nitrite and 20 g of water was dropwise added thereto over a period of 30 minutes at a reaction temperature of from 10 to 20° C. After the completion of the dropwise addition, stirring was carried out at the same temperature for 1 hour. After the completion of the reaction, neutralization in an aqueous sodium hydrogencarbonate solution was carried out, and extraction with methylene chloride was carried out. Methylene chloride was recovered, followed by distillation under reduced pressure to obtain 12.4 g of 2,6-difluorobenzyl alcohol (103° C./26 mmHg) (yield: 86.1%, purity: 88.1%).

Workup

  1. temperatureunder cooling
  2. temperatureThen, under cooling
  3. additionwas dropwise added
  4. additionAfter the completion of the dropwise addition
  5. waitwas carried out at the same temperature for 1 hour
  6. extractionextraction with methylene chloride
  7. customMethylene chloride was recovered
  8. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a84aad706d384dc2adff75e751c1d0fc
Source dataset
uspto-grants-2002_09
Patent number
US06452056B1

Reaction notes

Loading…