1,2-Dichlorobenzene → HCID 22459076, compound

HRID 613424Notes

Reaction equation

HRID 613424 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18]CC=C)=[CH:17][C:12]=3[O:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:23]1[CH:28]=CC=C[C:24]=1Cl>>[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([OH:18])=[C:17]([CH2:28][CH:23]=[CH2:24])[C:12]=3[O:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 22459113HCID 22459113, compound

Product 1

HCID 22459076HCID 22459076, compound

Conditions

Temperature
50 °C

Procedure

The product from Step D (1.245 grams), dissolved in 1,2-dichlorobenzene (20 mL) was refluxed under nitrogen for 11 hours. The solution was cooled to approx. 50° C. High vacuum was applied and the solvent removed until the residue solidified. The solid was dissolved in CH2Cl2 (100 mL), recovered, re-evaporated and chromatographed over silica gel (5:1 hex/ethyl acetate). Evaporation of the appropriate fractions gave the title compound as a pale yellow solid.

Workup

  1. temperaturewas refluxed under nitrogen for 11 hours
  2. customthe solvent removed until the residue solidified
  3. dissolutionThe solid was dissolved in CH2Cl2 (100 mL)
  4. customrecovered
  5. customre-evaporated
  6. customchromatographed over silica gel (5:1 hex/ethyl acetate)
  7. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-aef7d087ef50464aad3729bc749f51d5
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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