Sodium Hydroxide → 3'-Bromo-4'-(2-methylbutyloxy)-4-hydroxybiphenyl

HRID 648869Notes

Reaction equation

HRID 648869 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17](S(C3C=CC(C)=CC=3)(=O)=O)=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:13])[CH2:11][CH3:12].[OH-:30].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([OH:30])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:13])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 201440033'-Bromo-4'-(2-methylbutyloxy)-4-p-toluenesulfonylbiphenyl

Product 1

HCID 142048173'-Bromo-4'-(2-methylbutyloxy)-4-hydroxybiphenyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3'-bromo-4'-(2-methylbutyloxy)-4-p-toluenesulfonylbiphenyl (40 g) prepared in the above step (iii), a 50% aqueous solution (20 g) of NaOH and ethanol (350 ml) was heated under reflux for 4 hours, followed by distilling off ethanol, adding toluene, further adding 6N hydrochloric acid, separating the resulting liquid layer, washing with water to make the solution neutral, drying and distilling off toluene to obtain a raw product of oily 3'-bromo-4'-(2-methylbutyloxy)-4-hydroxybiphenyl, which was then dissolved in pyridine (200 ml), followed by adding benzoyl chloride (20 g), heating the mixture on a water bath, allowing to stand overnight, adding toluene, washing with 6N hydrochloric acid, washing with water, further washing with an aqueous solution of 2N NaOH, washing with water to make the solution neutral, drying and distilling off toluene to obtain 3'-bromo-4'-(2-methylbutyloxy)-4-biphenylylbenzoate (25 g). M.p.: 93.6° C.

Workup

  1. customprepared in the above step (iii)
  2. temperatureunder reflux for 4 hours
  3. distillationby distilling off ethanol
  4. additionadding toluene
  5. additionfurther adding 6N hydrochloric acid
  6. customseparating the resulting liquid layer
  7. washwashing with water
  8. customdrying
  9. distillationdistilling off toluene

Sources & evidence

ORD record
ord-07bd1717fd1d4d72a2145bfd5d3bfad1
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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