Hydrochloric Acid → HCID 69250530, compound

HRID 2220684Notes

Reaction equation

HRID 2220684 reaction equation
Br[C:2]1([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[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]([OH:37])=[CH:33][CH:32]=3)[C:3]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:4]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28112Lithium aluminum hydride2×HCID 69250567HCID 69250567, compound

Product 1

HCID 69250530HCID 69250530, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 54.15 g (0.1 mol) of 5-bromo-1,2,3,4-tetraphenyl-5-p-hydroxyphenylcyclopenta-1,3-diene in 300 ml of ether was added in portions to a suspension of 15.18 g (0.4 mol) of Li[AlH4] in 200 ml of ether with stirring. The slightly yellow-grey 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: 36.5 g (79%); elemental analysis: found: C, 90.04%, H, 5.56%. calculated: C, 90.88%, H, 5.67%).

Workup

  1. customThe slightly yellow-grey 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

Sources & evidence

ORD record
ord-9fbef4b7e82c404581a728b7effd8c40
Source dataset
uspto-grants-2008_08
Patent number
US07417247B2

Reaction notes

Loading…