Hydrochloric Acid → HCID 85958219, compound

HRID 2220677Notes

Reaction equation

HRID 2220677 reaction equation
Br[C:2]1([C:31]2[CH:36]=[CH:35][C:34]([CH:37]=[CH2:38])=[CH:33][CH:32]=2)[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:3]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Li+].[AlH4-].Cl>CCOCC>[C:7]1([C:6]2[CH:2]([C:31]3[CH:36]=[CH:35][C:34]([CH:37]=[CH2:38])=[CH:33][CH:32]=3)[C:3]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:4]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:5]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28112Lithium aluminum hydride2×HCID 69250590HCID 69250590, compound

Product 1

HCID 85958219HCID 85958219, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 55.1 g (0.1 mol) of 5-bromo-1,2,3,4-tetraphenyl-5-p-vinylphenylcyclopenta-1,3-diene in 300 ml of ether was added in portions to a suspension of 11.5 g (0.3 mol) of Li[AlH4] in 150 ml of ether with stirring. The slightly yellow-brown suspension formed was refluxed for 2 hours to complete the reduction. After cooling to room temperature, excess Li[AlH4] was hydrolyzed first with ice water (caution: vigorous H2 evolution) and then with dilute hydrochloric acid. All volatile organic components were then distilled off from the reaction mixture using a rotary evaporator. The slightly yellow crude product was filtered off with suction and washed several times with water. For further purification, it was dried azeotropically with toluene, filtered and recrystallized (yield: 39.65 g (84%); found: C, 94.09%, H, 5.81%. calculated: C, 94.03%, H, 5.97%).

Workup

  1. customThe slightly yellow-brown suspension formed
  2. temperaturewas refluxed for 2 hours
  3. distillationAll volatile organic components were then distilled off from the reaction mixture
  4. customa rotary evaporator
  5. filtrationThe slightly yellow crude product was filtered off with suction
  6. washwashed several times with water
  7. customFor further purification, it
  8. dry with materialwas dried azeotropically with toluene
  9. filtrationfiltered
  10. customrecrystallized (yield: 39.65 g (84%); found: C, 94.09%, H, 5.81%. calculated: C, 94.03%, H, 5.97%)

Sources & evidence

ORD record
ord-c41e926d033647f7904c7fad8eaa4b8d
Source dataset
uspto-grants-2008_08
Patent number
US07417247B2

Reaction notes

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