Ethyl Acetate → HCID 14750800, compound

HRID 2073299Notes

Reaction equation

HRID 2073299 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[C:14]([O:17][CH2:18][CH3:19])(=O)C>>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([C:4]2[CH:3]=[CH:19][C:18]([O:17][CH3:14])=[C:6]([O:8][CH3:9])[CH:5]=2)=[CH:3][C:4]=1[O:12][CH3:13])=[O:7]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 15128242Methyl 4-bromo-2-methoxybenzoate

Product 1

HCID 14750800HCID 14750800, compound

Procedure

A solution of 9.3 mL of 4-bromoveratrole in 200 mL of THF was cooled to -78° C. and 73 mL of 1.51M n-butyl lithium was added dropwise. The reaction mixture was stirred for 3 hours at -78° C. and a solution of freshly fused zinc chloride in 100 mL of THF was added. After 1 hour, this solution was added to a second solution formed by treatment of a suspension of 1.7 g of bis(triphenylphosphine)palladium dichloride in 300 mL of THF with 4.9 mL of a 1M solution of diisobutylaluminum hydride in hexane followed by addition of 16.2 g of methyl 4-bromo-2-methoxybenzoate using a double tipped syringe needle. The reaction mixture was allowed to stir at room temperature over night and was diluted with ethyl acetate. The organic solution was washed with 1M HCl, water, and brine, dried, and evaporated to a dark oil which was purified by preparative hplc eluting with 3:1 hexane:ethyl acetate and crystallized from ethyl acetate-hexane to give 8.4 g 3,3',4'-trimethoxy[1,1'-biphenyl]-4-carboxylic acid methyl ester. mp 96°-97.5° C.

Workup

  1. washThe organic solution was washed with 1M HCl, water, and brine
  2. customdried
  3. customevaporated to a dark oil which
  4. customwas purified by preparative hplc
  5. washeluting with 3:1 hexane
  6. customethyl acetate and crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0e1834d1f18e423c8a8c47e3a93377b3
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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