Water → HCID 178521543, compound

HRID 1388246Notes

Reaction equation

HRID 1388246 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11](CC([O-])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:18].[Na+].O.C1(C)C=CC=CC=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([OH:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1140TolueneHCID 14798Sodium HydroxideHCID 178525541HCID 178525541, compound

Product 1

HCID 178521543HCID 178521543, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture (208.5 g) of the compound (X1) and the compound (X11) obtained in Step E was dissolved in ethanol (460 ml), and a solution of NaOH (28 g) and water (30 ml) was added and the mixture was heated, followed by reflux for one hour. After cooling, toluene (500 ml) and water (500 ml) were added, and the resulting toluene layer was washed with 2 N--NaOH aqueous solution and further with water till the layer became neutral. After removing toluene by concentration of the layer, the resulting raw crystals were recrystallized from ethyl acetate (130 ml) to obtain trans-4-(p-bromophenyl)-cyclohexanol (X11) (130 g) having a melting point of 109.5°~111.0° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureby reflux for one hour
  3. temperatureAfter cooling
  4. washthe resulting toluene layer was washed with 2 N
  5. customAfter removing toluene by concentration of the layer
  6. customthe resulting raw crystals were recrystallized from ethyl acetate (130 ml)

Sources & evidence

ORD record
ord-8f97b7a8358840c1981ab529baba3342
Source dataset
uspto-grants-1984_02
Patent number
US04431564

Reaction notes

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