4'-Hydroxy-4-biphenylcarboxylic acid → HCID 14495469, compound

HRID 2307615Notes

Reaction equation

HRID 2307615 reaction equation
[CH3:1][O-:2].[Na+].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>CO>[CH2:1]([O:2][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)=[CH:19][CH:18]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 10942334Sodium Methoxide

Product 1

HCID 14495469HCID 14495469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.25 g of methanol solution including 28% sodium methylate was added to 2.50 g of 4-(4-hydroxyphenyl)benzoic acid suspended in 10 ml of methanol. After the mixture was stirred for 5 minutes, it was concentrated under reduced pressure. 10 ml of N,N-dimethylformamido and 2.43 g of benzyl-bromoamide were added to the residue. The mixture was stirred during night at room temperature and poured into 30 ml of ice water, and extracted with 50 ml of toluene. The organic layer was washed with in order saturated sodium hydrogen and water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. Obtained crude crystals were purified by silica gel column chromatography with toluene-ethyl acetate eluent, and hexane was added to them. Precipitated crystals were collected by filtration, and washed with hexane. 4-(4-hydroxyphenyl)benzoate benzylester 2.60 g was obtained.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. addition10 ml of N,N-dimethylformamido and 2.43 g of benzyl-bromoamide were added to the residue
  3. stirringThe mixture was stirred during night at room temperature
  4. additionpoured into 30 ml of ice water
  5. extractionextracted with 50 ml of toluene
  6. washThe organic layer was washed with in order saturated sodium hydrogen and water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customObtained crude crystals
  10. customwere purified by silica gel column chromatography with toluene-ethyl acetate eluent, and hexane
  11. additionwas added to them
  12. customPrecipitated crystals
  13. filtrationwere collected by filtration
  14. washwashed with hexane

Sources & evidence

ORD record
ord-8b20571ac871465a9dc4fa2e79a56da4
Source dataset
uspto-grants-2004_12
Patent number
US06831190B1

Reaction notes

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