N-bromobutanimide → 2-(4-Methylphenyl)benzoic acid

HRID 2427897Notes

Reaction equation

HRID 2427897 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:2].BrN1C(=[O:22])CCC1=O>ClCCl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[C:3]([C:1]([OH:22])=[O:2])=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13940094'-Methyl[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 815682-(4-Methylphenyl)benzoic acidYield 134.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-formylphenyl)toluene (2 g, 10.2 mmol), N-bromosuccinimide (1.8 g, 10.1 mmol) and dibenzoyl peroxide 75% (0.26 g, 0.8 mmol) in 22 ml of dichloromethane is stirred at the temperature of reflux for 5 hours. Reaction mixture is filtered and evaporated to dryness under reduced pressure. Oily residue is suspended in 20 ml of brine and extracted with 20 ml of ethyl acetate. Organic layer is evaporated to dryness under reduced pressure to obtain 2.88 g of oily product.

Workup

  1. temperatureof reflux for 5 hours
  2. customReaction mixture
  3. filtrationis filtered
  4. customevaporated to dryness under reduced pressure
  5. extractionextracted with 20 ml of ethyl acetate
  6. customOrganic layer is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e7b9a2ccef8942bcbb34a3e5a76e4024
Source dataset
uspto-grants-2011_06
Patent number
US07968727B2

Reaction notes

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