Hydrogen Peroxide → 3,3',5'-Trimethyl[1,1'-biphenyl]-2-carboxylic acid

HRID 1918433Notes

Reaction equation

HRID 1918433 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)[C:3]=1[CH:16]=[O:17].OO.[O-:20]Cl=O.[Na+]>C(#N)C.[O-]S([O-])=O.[Na+].[Na+]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=2)[C:3]=1[C:16]([OH:20])=[O:17]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 23668197Sodium ChloriteHCID 57909133HCID 57909133, compound

Product 1

HCID 532252823,3',5'-Trimethyl[1,1'-biphenyl]-2-carboxylic acidYield 106.8%

Reagents, catalysts & solvents 2

HCID 24437Sodium SulfiteCatalystHCID 6342AcetonitrileSolvent

Procedure

The aldehyde 51 (2.75 g, 11.5 mmol) was dissolved in acetonitrile (18 ml, technical grade). NaH2PO4 (0.453 g, dissolved in 5.5 ml H2O) and H2O2 (1.93 ml of a 30% solution) was added. The reaction mixture was cooled to 0° C. (with ice/water) and NaClO2 (2.2 g, dissolved in 19 ml water) was added within 60 min via a syringe. The solution was allowed to warm to ambient temperature and was stirred for additional 3.5 h. Then Na2SO3 (100 mg) was added, stirred for 5 min. After treatment with HCl (50 ml of a 10% solution) the reaction mixture was extracted with ether (3×75 ml). The combined organic phase was extracted with NaOH (4×75 ml, 1 N). The combined NaOH layers were acidified with HCl to pH 1 and extracted again with Et2O. The combined organic layers were dried over MgSO4 and the volatiles removed in vacuo to afford 52 (2.95 g, quant.) as a colorless oil. The product was used without any further purification.

Workup

  1. additionwas added within 60 min via a syringe
  2. stirringstirred for 5 min
  3. extractionAfter treatment with HCl (50 ml of a 10% solution) the reaction mixture was extracted with ether (3×75 ml)
  4. extractionThe combined organic phase was extracted with NaOH (4×75 ml, 1 N)
  5. extractionextracted again with Et2O
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-c086d84216fb467eb713367a0d69e4ea
Source dataset
uspto-grants-2013_12
Patent number
US08618328B2

Reaction notes

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