Chlorodifluoromethane → HCID 53951435, compound

HRID 361968Notes

Reaction equation

HRID 361968 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([OH:12])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])=[O:5].[OH-].[Na+].Cl[CH:24]([F:26])[F:25]>C(COC)OC.O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([O:12][CH:24]([F:26])[F:25])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[CH3:15])=[O:5]

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 53938437HCID 53938437, compound

Product 1

HCID 53951435HCID 53951435, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,6-dichloro-5'-hydroxy-4'-methoxy-2'-methyl-benzophenone (1.0 g; 3.2 mmol) in dimethoxyethane (7 ml) a solution of sodium hydroxide(0.6 g; 15 mmol) in water (1 ml) is added. The mixture is-heated to 60° C. with stirring, then a stream of chlorodifluoromethane is introduced for 20 minutes. After further stirring for 1.5 hours the solvent is evaporated. The residue is extracted with a mixture of trichloromethane and water. The organic phase is separated, dried and the solvent is evaporated. For purification, a flash column with silicagel (30g) is used (elution with mixtures of petrolether/ethylacetate 9:1, then 8:2, then 7:3 (v/v)). The resulting compound forms white crystals (0.6 g; 5.8% y); mp. 126°-128° C.

Workup

  1. stirringAfter further stirring for 1.5 hours the solvent
  2. customis evaporated
  3. extractionThe residue is extracted with a mixture of trichloromethane and water
  4. customThe organic phase is separated
  5. customdried
  6. customthe solvent is evaporated
  7. customFor purification
  8. washelution with mixtures of petrolether/ethylacetate 9:1

Sources & evidence

ORD record
ord-9a3dda8fcaa34b6db286e515c4201983
Source dataset
uspto-grants-1999_02
Patent number
US05866722

Reaction notes

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