Hydrochloric Acid → HCID 178444262, compound

HRID 1936323Notes

Reaction equation

HRID 1936323 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[CH2:10][CH2:11][CH2:12][CH3:13].Cl>C(Cl)Cl>[C:5]([C:29]1[CH:30]=[CH:31][C:26]([C:23]2[CH:22]=[CH:21][C:20]([C@H:17]3[CH2:18][CH2:19][C@H:14]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:15][CH2:16]3)=[CH:25][CH:24]=2)=[CH:27][CH:28]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178444253HCID 178444253, compound

Product 1

HCID 178444262HCID 178444262, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

First, 23.6 g of anhydrous aluminum chloride and 120 ml of methylene chloride were put in a 300 ml flask. After 14.0 g of acetyl chloride was dropped into the mixture at 5° C. or less, the resultant mixture was stirred keeping the same temperature for 30 minutes. Then, 45.2 g of 4-(trans-4-pentylcyclohexyl)biphenyl was added to resultant mixture at 5° C. or less and stirred for 30 minutes at room temperature. After the reaction, the reaction solution was poured into dilute hydrochloric acid, and an organic layer was separated. The organic layer was then washed with water and dried with sodium sulfate. The solvent was then distilled off. The residue was recrystallized from acetone to obtain 24.0 g (Y: 46.0%) of 4-acetyl-4′-(trans-4-pentylcyclohexyl)biphenyl. The purity of the resultant compound was 99.7% as measured by GC.

Workup

  1. customfor 30 minutes
  2. customAfter the reaction
  3. customan organic layer was separated
  4. washThe organic layer was then washed with water
  5. dry with materialdried with sodium sulfate
  6. distillationThe solvent was then distilled off
  7. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-c808bb0317524183bb7162557f29ab15
Source dataset
uspto-grants-2002_05
Patent number
US06388146B1

Reaction notes

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