Hydrochloric Acid → HCID 20340704, compound

HRID 442241Notes

Reaction equation

HRID 442241 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21]1([CH3:30])[CH:26]=[CH:25][CH:24]=[C:23]([C:27](Cl)=[O:28])[CH:22]=1.Cl>ClCCCl>[CH3:30][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[C:27]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:27](=[O:28])[C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([CH3:30])[CH:22]=3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77131,2-DiphenoxyethaneHCID 743753-Methylbenzoyl chloride2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 20340704HCID 20340704, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of anhydrous aluminum chloride (24 g) in 300 ml dry 1,2-dichloroethane is added 1,2-diphenoxyethane (17.8 g, 0.083 mole) at room temperature. To this mixture is added over a period of 30 minutes m-toluoyl chloride (27 g, 0.17 mole). The temperature of the reaction rises to 40° (all temperatures are Centigrade) and hydrogen chloride gas evolves from the mixture. Following the addition of the m-toluoyl chloride the reaction is externally heated to 65° plus or minus 3°. This temperature and stirring are maintained for 22 hours. The mixture is then allowed to cool to room temperature and poured on 1 kg of crushed ice to destroy the aluminum chloride complex. The ice is allowed to melt and the water separates from the organic layer. The latter is washed twice with 200 ml of 10% hydrochloric acid, three times with water and the solvent removed by distillation. The residual crude crystals are crystallized from dichloroethane, yield 15.9 g (43%) mp 164° - 167°. Calculated for C30H26O4 : C, 79.98%; H, 5.82%. Found: C, 79.65%; H, 5.88%.

Workup

  1. customrises to 40°
  2. temperatureis externally heated to 65°
  3. custom3°
  4. temperatureare maintained for 22 hours
  5. customto destroy the aluminum chloride complex
  6. washThe latter is washed twice with 200 ml of 10% hydrochloric acid, three times with water
  7. customthe solvent removed by distillation
  8. customThe residual crude crystals are crystallized from dichloroethane, yield 15.9 g (43%) mp 164° - 167°

Sources & evidence

ORD record
ord-d4e7f1b15b464757a8f3a90b9b0b9299
Source dataset
uspto-grants-1977_08
Patent number
US04044139

Reaction notes

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