1,2-Dichloroethane → HCID 54568949, compound

HRID 846219Notes

Reaction equation

HRID 846219 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Al+3].[Cl-].[Cl-].[Cl-].[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14]1.Cl[CH2:21]CCl>>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([C:16](=[O:17])[CH2:15][CH2:14][C:13]([O:18][CH3:21])=[O:19])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 7922Succinic anhydrideHCID 97072-FluorophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54568949HCID 54568949, compound

Conditions

Temperature
85 °C

Procedure

To a solution of 2-fluorophenol (22.4 g, 200 mmole) in 1,2-dichloroethane (250 ml) at 0° there was added AlCl3 (54 g, 400 mmole) and then succinic anhydride (20 g, 200 mmole). The reaction mixture was heated at 85° C. for 18 hours, then cooled, poured on ice and stirred for several hours at room temperature. The layers were separated and the aqueous layers extracted with CH2Cl2. The combined extracts were washed with water, dried (MgSO4) and evaporated to a semi-solid which was taken up in a solution of methanolic HCl (500 ml, approximately 3N). After standing for 24 hours the solution was poured into water, extracted with CH2Cl2, washed with water, dried and evaporated to a small volume. The crude product was purified by chromatography on silica gel to yield the title compound.

Workup

  1. temperaturecooled
  2. additionpoured on ice
  3. customThe layers were separated
  4. extractionthe aqueous layers extracted with CH2Cl2
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to a semi-solid which
  8. additionthe solution was poured into water
  9. extractionextracted with CH2Cl2
  10. washwashed with water
  11. customdried
  12. customevaporated to a small volume
  13. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2ec14defcbbc4deb9a279b3ecb5afe6e
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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