1,3-Dichlorobenzene → HCID 20315348, compound

HRID 2419336Notes

Reaction equation

HRID 2419336 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[O:13]1[CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14]1>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:8])[CH:5]=[CH:6][C:7]=1[CH:18]([CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14][OH:13]

Participants

5

Reactant 3

HCID 109431,3-DichlorobenzeneHCID 150362-ButyloxiraneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20315348HCID 20315348, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A slurry of m-dichlorobenzene, 735 g. (5.0 mole) and anhydrous aluminum chloride, 162 g. (1.1 mole) is cooled to 10° using an ice-water bath and 1,2-epoxyhexane, 100 g. (1.0 mole) is added dropwise over a 1 hour period. The temperature of the reaction is kept below 15°. The reaction mixture is allowed to come to room temperature and stirring is continued overnight. The reaction mixture is then poured into a 4 liter flask containing ice and concentrated hydrochloric acid (50 ml) with stirring. The aqueous and organic layers are separated and the aqueous layer extracted three times with ether (150 ml). The combined organic extracts are washed twice with water (50 ml) and dried over magnesium sulfate. Solvent is evaporated and vacuum distillation (160°-172°/0.1 mm) gives 114 g. (46%) of product.

Workup

  1. temperature(1.1 mole) is cooled to 10°
  2. addition(1.0 mole) is added dropwise over a 1 hour period
  3. customis kept below 15°
  4. customto come to room temperature
  5. additionThe reaction mixture is then poured into a 4 liter flask
  6. stirringwith stirring
  7. customThe aqueous and organic layers are separated
  8. extractionthe aqueous layer extracted three times with ether (150 ml)
  9. washThe combined organic extracts are washed twice with water (50 ml)
  10. dry with materialdried over magnesium sulfate
  11. customSolvent is evaporated
  12. distillationvacuum distillation (160°-172°/0.1 mm)
  13. customgives 114 g

Sources & evidence

ORD record
ord-1db14a8b88814b508a0e66649a54930c
Source dataset
uspto-grants-1978_08
Patent number
US04105762

Reaction notes

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