2-Bromoethanol → HCID 178447913, compound

HRID 1906700Notes

Reaction equation

HRID 1906700 reaction equation
Br[CH2:2][CH2:3][OH:4].[CH2:5]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[CH2:6][CH3:7].[OH-].[K+]>C(O)C.O>[OH:4][CH2:3][CH2:2][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:11]2[CH2:10][CH2:9][C@H:8]([CH2:5][CH2:6][CH3:7])[CH2:13][CH2:12]2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 14797Potassium HydroxideHCID 178447901HCID 178447901, compound

Product 1

HCID 178447913HCID 178447913, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Bromo-1-ethanol (5.0 g, 0.04 mol) and 4-(trans-4-propylcyclohexyl)phenol (4.4 g, 0.02 mol) were dissolved in ethanol (300 ml) and agitated at room temperature. To this solution was gradually dropwise added a solution of KOH (10 g) in water (20 ml), over 30 minutes, followed by stirring for 40 hours, distilling off about 200 ml of ethanol under reduced pressure, adding water (500 ml) to deposit solids, separating the solids from liquid, dissolving them in toluene (100 ml), filtering off insoluble matter, washing the toluene solution twice with 2N-NaOH, then three times with water, drying over anhydrous sodium sulfate, distilling off toluene and recrystallizing the resulting crystals from n-heptane to obtain the objective 1-(2-hydroxyethoxy)-4-(trans-4-propylcyclohexyl)benzene. Yield: 1.8 g (34%). C-S: 71.5° C. S-I: 81.4° C.

Workup

  1. stirringby stirring for 40 hours
  2. distillationdistilling off about 200 ml of ethanol under reduced pressure
  3. additionadding water (500 ml)
  4. customseparating the solids from liquid
  5. dissolutiondissolving them in toluene (100 ml)
  6. filtrationfiltering off insoluble matter
  7. washwashing the toluene solution twice with 2N-NaOH
  8. dry with materialthree times with water, drying over anhydrous sodium sulfate
  9. distillationdistilling off toluene
  10. customrecrystallizing the resulting crystals from n-heptane

Sources & evidence

ORD record
ord-8e6247b16a9344a5b96bb43515c9a419
Source dataset
uspto-grants-1987_03
Patent number
US04654162

Reaction notes

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