Dichlorophen → 2,10-dichloro-12H-dibenzo[d,g][1,3]dioxocine

HRID 1060850Notes

Reaction equation

HRID 1060850 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH2:8][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[OH:16])[CH:7]=1.I[CH2:19]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][CH2:19][O:16][C:10]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=3[CH2:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 3037DichlorophenHCID 6346DiiodomethaneHCID 11430Potassium Carbonate

Product 1

HCID 149005562,10-dichloro-12H-dibenzo[d,g][1,3]dioxocineYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of bis-(5-chloro-2-hydroxyphenyl)-methane (24.4 g, 90.7 mmol) in dry DMF (340 mL) was added diiodomethane (25.5 g, 95.0 mmol) and potassium carbonate (18.2 g, 132 mmol). The mixture was stirred at 105° C. for 16 h. The mixture was added to ice water (1200 mL) and stirred for 30 min. The product was isolated by filtration, and washed with water and suspended in a mixture of ethanol (200 mL) and 4N NaOH (50 mL). The mixture was heated at 80° C. for 1 h. The mixture was added to water (600 mL) and 21.45 g (84%) 2,10-dichloro-12H-dibenzo[d,g][1,3]-dioxocin was isolated by filtration.

Workup

  1. stirringstirred for 30 min
  2. customThe product was isolated by filtration
  3. washwashed with water
  4. additionsuspended in a mixture of ethanol (200 mL) and 4N NaOH (50 mL)
  5. temperatureThe mixture was heated at 80° C. for 1 h
  6. additionThe mixture was added to water (600 mL)

Sources & evidence

ORD record
ord-5114b1d9bf3f4fed9406551a0f78af37
Source dataset
uspto-grants-2003_02
Patent number
US06525086B2

Reaction notes

Loading…