Carbon Dioxide → 3.5-Diethyl-4-methoxybenzoic acid

HRID 1280923Notes

Reaction equation

HRID 1280923 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 3h, 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. concentrationconcentrated
  2. filtrationfiltered
  3. washthe collected solids washed with H2O
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-e3c8481213fe4d79a6a2015c8e1d7e4c
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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