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

HRID 648870Notes

Reaction equation

HRID 648870 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2C2C=CC(C([O-])=O)=CC=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:13])[CH2:11][CH3:12].[OH-:29].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([OH:29])=[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 86742091HCID 86742091, compound

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-biphenylylbenzoate (4.8 g) from step (IV), a 40% aqueous solution (3.2 g) of NaOH and ethanol (100 ml) was heated under reflux for 3 hours, followed by distilling off ethanol, adding toluene, acidifying with 6N hydrochloric acid, heating to dissolve insolubles, separating the solution layer, washing with water, further washing with an aqueous solution of sodium hydrogen sulfite, washing with water to make the solution neutral, drying, distilling off toluene and recrystallizing the residue from n-heptane to obtain 3'-bromo-4'-(2-methylbutyloxy)-4-hydroxybiphenyl (3.0 g). M.p.: 75°~76.5° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationby distilling off ethanol
  3. additionadding toluene
  4. temperatureheating
  5. dissolutionto dissolve insolubles
  6. customseparating the solution layer
  7. washwashing with water
  8. washfurther washing with an aqueous solution of sodium hydrogen sulfite
  9. washwashing with water
  10. customdrying
  11. distillationdistilling off toluene
  12. customrecrystallizing the residue from n-heptane

Sources & evidence

ORD record
ord-62a4d89c856448c5b5589cbfbcc1e0a4
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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