Carbon Dioxide → 3',5-Dimethoxy[1,1'-biphenyl]-2-carboxylic acid

HRID 1871629Notes

Reaction equation

HRID 1871629 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][CH:11]=1.C([Li])(C)(C)C.[C:23](=[O:25])=[O:24].Cl>CN(C)C=O.CCOCC.O>[C:23]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][CH:11]=1)([OH:25])=[O:24]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 115728962-bromo-5,3'-dimethoxybiphenylHCID 178418306HCID 178418306, compound

Product 1

HCID 134616943',5-Dimethoxy[1,1'-biphenyl]-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
-60 °C

Procedure

12.1 g of 2-bromo-5,5'-dimethoxybiphenyl was dissolved in 100 mL of dry dimethylformamide and the resulting solution was cooled to -60° C. under nitrogen. 55 mL of 1.7 M t-butyllithium in hexanes was added over a 20-minute period. The resulting solution was transferred to another flask containing a mixture of 275 mL of ether and dry ice which effected a lot of gas evolution. The mixture was allowed to warm to room temperature over a 3-hour period during which time a white precipitate had formed. The mixture was diluted with ether and treated with dilute hydrochloric acid and water. The organic layer was separated and the solvents were removed under reduced pressure to yield a yellow oil. Hexanes were added to the oil causing a solid to precipitate out. The solids were filtered and stirred in a 60:40% ether-hexane mixture to remove impurities. The solid was filtered and dried in vacuo to yield 7.82 g of 2-carboxy-5,5'-dimethoxybiphenyl as an off-white solid. The structure was confirmed by NMR and infrared spectroscopy.

Workup

  1. customThe resulting solution was transferred to another flask
  2. additioncontaining
  3. temperatureto warm to room temperature over a 3-hour period during which time a white precipitate
  4. customhad formed
  5. customThe organic layer was separated
  6. customthe solvents were removed under reduced pressure
  7. customto yield a yellow oil
  8. customto precipitate out
  9. filtrationThe solids were filtered
  10. custom40% ether-hexane mixture to remove impurities
  11. filtrationThe solid was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-0ced2dbdf542450cb3d29d73d9d439b7
Source dataset
uspto-grants-2000_08
Patent number
US06103912

Reaction notes

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