Benzene → Benzoic Acid

HRID 1272571Notes

Reaction equation

HRID 1272571 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1C=CC=CC=1.[Li].CC(C)([O-])C.[K+].C1(C2C=CC=CC=2)C=CC=CC=1.[C:33](=[O:35])=[O:34]>C1COCC1>[C:33]([OH:35])(=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 241BenzeneHCID 280Carbon DioxideHCID 7095BiphenylHCID 10952Chlorocyclohexane2×HCID 3028194LithiumHCID 23665647Potassium tert-butoxide

Product 1

HCID 243Benzoic AcidYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.2 mol of chlorocyclohexane and 0.2 mol of benzene is added dropwise to a suspension of 0.4 mol of lithium granules, 0.21 mol of potassium tert-butoxide and 35 mg of biphenyl in 300 g of THF at −72° C. After a conversion of the chlorocyclohexane of >97% determined by means of GC (total of 24 h), carbon dioxide is passed in until saturation is achieved. The work-up is carried out by a method analogous to that in example 3; benzoic acid is obtained in a yield of 79%.

Sources & evidence

ORD record
ord-7081cbcce93e40fca41d24fe12fd85a3
Source dataset
uspto-grants-2007_04
Patent number
US07208614B2

Reaction notes

Loading…