Anthracene → CID 10867395

HRID 1369183Notes

Reaction equation

HRID 1369183 reaction equation
[Mg:1].[CH:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1>C1COCC1.BrCCBr>[CH:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:2]=[CH:3][CH:4]=1.[Mg:1]

Participants

5

Reactant 2

HCID 8418AnthraceneHCID 5462224Magnesium

Product 1

HCID 10867395CID 10867395

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.7 g (110 mmol) of magnesium turnings were added to a solution of 2 g (11 mmol) of anthracene in 100 ml of THF, and a few drops of 1,2-dibromoethane were added. After the mixture had been stirred at room temperature for about 2 hours, the bright orange precipitate of magnesium anthracene had formed. A solution of 19 g (100 mmol) of 4-chlorobenzaldehyde dimethyl acetal in 100 ml of THF was added to the refluxing suspension over the course of 1 hour. After the mixture had refluxed for 4 hours, the yield of Mg 4-chlorobenzaldehyde dimethyl acetal according to GC analysis (determined as benzaldehyde after hydrolysis using dilute HCl) was 90%.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-693242eb204c4b3e9f5f35d08ace2259
Source dataset
uspto-grants-2003_06
Patent number
US06576789B1

Reaction notes

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