Carbon Dioxide → 3.5-Diethyl-4-methoxybenzoic acid

HRID 1871333Notes

Reaction equation

HRID 1871333 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([CH2:12][CH3:13])[CH:3]=1.C([Li])CCC.[C:19](=[O:21])=[O:20]>C1COCC1.CCOC(C)=O>[CH2:12]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][CH3:9])[C:5]=1[O:10][CH3:11])[C:19]([OH:21])=[O:20])[CH3:13]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 234456364-Bromo-2,6-diethylanisoleHCID 178418339Butyllithium

Product 1

HCID 234456633.5-Diethyl-4-methoxybenzoic acidYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

At -78° C., to a stirred solution of 4-bromo-2,6-diethylanisole (12.0 g, 49.4 mmol) in THF (329 mL) was added dropwise n-butyllithium (27.2 mL, 43.5 mmol). After 3 h, the reaction was poured into crushed dry ice and allowed to warm to ambient temperature. The reaction mixture was diluted with EtOAc, concentrated, suspended in H2O, acidified (pH 1), filtered and the collected solids washed with H2O. The crude product was slurried in hexane (15 mL), collected by filtration and dried to give 6.76 g (66%) of the title compound. 1H NMR: consistent. IR (KBr) consistent. mass spectrum (EI), m/z 208 (M+). Anal. Calcd. for C12H16O3 : C, 69.21; H, 7.74; N, 0.00. Found: C, 69.28; H, 7.49; N, 0.07.

Workup

  1. additionthe reaction was poured
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washthe collected solids washed with H2O
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-31dcddf584df4d3bbb1e4cf89bfbc2a5
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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