4-Bromophenol → HCID 14422829, compound

HRID 1639060Notes

Reaction equation

HRID 1639060 reaction equation
[OH-].[Na+].Cl[CH2:4][CH:5]([OH:9])[CH2:6][CH2:7][Cl:8].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1>O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:4][CH:5]([OH:9])[CH2:6][CH2:7][Cl:8])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 14798Sodium Hydroxide2×HCID 170211,4-Dichloro-2-butanol

Product 1

HCID 14422829HCID 14422829, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a rapidly stirring solution of 22.5 g (0.56 mole) of sodium hydroxide in 400 ml of water was added, dropwise, 73.8 g (0.52 mole) of freshly distilled 1,4-dichloro-2-butanol. The mixture was stirred for 15 min at ambient temperature. To this mixture was added, over a 45 min period, a solution obtained by adding 75.0 g (0.43 mole) of 4-bromophenol to a solution of 18.0 g (0.47 mole) of sodium hydroxide in 430 ml of water. The mixture was stirred vigorously for 30 hr and then cooled in an ice bath. The suspended solid was collected by filtration, rinsed with water several times and air dried. Recrystallization from ethyl ether-petroleum ether (b.p. range 30°-60° C.) gave 44.2 g (37%) of white solid, m.p. 75°-78° C.

Workup

  1. additionTo this mixture was added, over a 45 min period
  2. customa solution obtained
  3. stirringThe mixture was stirred vigorously for 30 hr
  4. temperaturecooled in an ice bath
  5. filtrationThe suspended solid was collected by filtration
  6. washrinsed with water several times and air
  7. customdried
  8. customRecrystallization from ethyl ether-petroleum ether (b.p. range 30°-60° C.)

Sources & evidence

ORD record
ord-a45f12cf49db40f2afdd8adbb8d0d550
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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