Sulfuric Acid → Ethyl 4'-hydroxy-4-biphenylcarboxylate

HRID 1062353Notes

Reaction equation

HRID 1062353 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[CH3:22][CH2:23]CCCC>C(O)C>[CH2:22]([O:18][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][C:13]([C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)=[CH:14][CH:15]=1)[CH3:23]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8058HexaneHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 4049156Ethyl 4'-hydroxy-4-biphenylcarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At room temperature, 0.7 ml of concentrated sulfuric acid was added to 5.00 g of 4-(4-hydroxyphenyl)benzoic acid suspended in 50 ml of ethanol. After the mixture was refluxed with heating for 7 hours, the mixture was concentrated under reduced pressure. Water and ethyl acetate were added to the residue, and then the organic layer was washed in order with water, saturated sodium hydrogen carbonate and saturated sodium chloride solution. And it was 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. Obtained crystals were dispersed by hexane and collected by filtration and washed with hexane. 4-(4-hydroxyphenyl)benzoate ethylester 5.04 g was obtained.

Workup

  1. temperatureAfter the mixture was refluxed
  2. temperaturewith heating for 7 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. washthe organic layer was washed in order with water, saturated sodium hydrogen carbonate and saturated sodium chloride solution
  6. dry with materialAnd it was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customObtained crude crystals
  9. customwere purified by silica gel column chromatography with toluene-ethyl acetate eluent
  10. customObtained crystals
  11. filtrationcollected by filtration
  12. washwashed with hexane

Sources & evidence

ORD record
ord-5e5f30c4f086462eb43e17ddab85c724
Source dataset
uspto-grants-2005_11
Patent number
US06960681B2

Reaction notes

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