HCID 11068212, compound → HCID 15656407, compound

HRID 2421280Notes

Reaction equation

HRID 2421280 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]CC)=[O:23])=[CH:18][CH:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

3

Reactant 1

HCID 11068212HCID 11068212, compound

Product 1

HCID 15656407HCID 15656407, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

5.0 g (1.41 mmol) of ethyl 3′,5′-ditert-butyl-4′-hydroxy-1,1′-biphenyl-4-carboxylate (Chem. Lett. (1998), 9, 931-932) is dissolved in ethanol (25 ml). The solution is cooled down to 0° C. then a 1N solution of soda is added dropwise. After stirring overnight at ambient temperature, the reaction medium is heated under reflux in order to complete the reaction. After evaporation of the solvents and dilution of the residue with water, the mixture obtained is acidified with a 1N solution of HCl and extraction is carried out with dichloromethane. The organic phase is washed with sodium chloride in a saturated aqueous solution before being dried over magnesium sulphate, filtered and concentrated under vacuum. The product obtained is purified by crystallization from diisopropyl ether in order to produce a yellow-white solid with a yield of 47%. Melting point: >240° C.

Workup

  1. temperaturethe reaction medium is heated
  2. temperatureunder reflux in order
  3. customthe reaction
  4. customAfter evaporation of the solvents and dilution of the residue with water
  5. customthe mixture obtained
  6. extractionis acidified with a 1N solution of HCl and extraction
  7. washThe organic phase is washed with sodium chloride in a saturated aqueous solution
  8. dry with materialbefore being dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe product obtained
  12. customis purified by crystallization from diisopropyl ether in order
  13. customto produce a yellow-white solid with a yield of 47%

Sources & evidence

ORD record
ord-823aa343bfcb4d7e9b2988fa317cce2c
Source dataset
uspto-grants-2011_06
Patent number
US07956075B2

Reaction notes

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