Methanol → HCID 69247959, compound

HRID 2220682Notes

Reaction equation

HRID 2220682 reaction equation
[C:1]1([C:7]2[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)(O)[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:9]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:8]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Br:42])(=O)C.CO>C1(C)C=CC=CC=1>[Br:42][C:11]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10482Acetyl bromideHCID 69250045HCID 69250045, compound

Product 1

HCID 69247959HCID 69247959, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

54.19 g (0.11 mol) of 1,2,3,4-tetraphenyl-5-p-methoxyphenylcyclopenta-1,3-dien-5-ol were suspended in 300 ml of toluene. 74 g (0.6 mol) of acetyl bromide were added dropwise in the course of 20 minutes at room temperature and the reaction batch was then refluxed for 2 hours. Toward the end of the reaction, 2 ml of methanol were also added dropwise. Excess acetyl bromide and toluene were distilled off in vacuo. The remaining oil crystallized after addition of 100 ml of petroleum ether. The orange precipitate was filtered off with suction, rinsed with petroleum ether and dried. The product was used for the further syntheses. Analytically pure orange product was obtained by recrystallization from toluene. (Yield: 54. 32 g (89%); elemental analysis for C36H27OBr: found: C, 77.06%, H, 4.90%. calculated: C, 77.84%, H, 4.90%).

Workup

  1. temperaturethe reaction batch was then refluxed for 2 hours
  2. additionwere also added dropwise
  3. distillationExcess acetyl bromide and toluene were distilled off in vacuo
  4. customThe remaining oil crystallized
  5. additionafter addition of 100 ml of petroleum ether
  6. filtrationThe orange precipitate was filtered off with suction
  7. washrinsed with petroleum ether
  8. customdried
  9. customAnalytically pure orange product was obtained by recrystallization from toluene

Sources & evidence

ORD record
ord-320213cb49ba4d1085931435bd41dff8
Source dataset
uspto-grants-2008_08
Patent number
US07417247B2

Reaction notes

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