Hydrochloric Acid → 4-Formyl-2-methylbenzoic acid

HRID 1037017Notes

Reaction equation

HRID 1037017 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[Li]CCCC.CN([CH:20]=[O:21])C.Cl>C1COCC1>[CH:20]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 995704-Bromo-2-methylbenzoic acidHCID 178418339Butyllithium

Product 1

HCID 207748714-Formyl-2-methylbenzoic acidYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-methylbenzoic acid (10.7 g, 50 mmol) in THF (250 mL) at −78° C. was added n-BuLi (60 mL, 2.5 M in hexane). The mixture was stirred for 3 h and to it was added DMF (9.6 mL, 125 mmol). The reaction mixture was stirred for 1.5 h, acidified with 1N HCl and extracted with EA (200 mL). The organic solution was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude yellow solid was washed with PE to afford 4-formyl-2-methylbenzoic acid (3.4 g; yield 41%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 1.5 h
  2. extractionextracted with EA (200 mL)
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe crude yellow solid was washed with PE

Sources & evidence

ORD record
ord-fa38128bbae541e28234a1888315657a
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

Loading…