3-Bromo-1-propanol → 1-[4-(3-Hydroxypropyloxy)phenyl]propan-2-one

HRID 851180Notes

Reaction equation

HRID 851180 reaction equation
C1[O:14][C:4]([CH3:13])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)OC1.[OH-].[Na+].Br[CH2:18][CH2:19][CH2:20][OH:21]>O>[OH:21][CH2:20][CH2:19][CH2:18][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:14])[CH3:13])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 14798Sodium HydroxideHCID 566304374-Hydroxyphenylpropan-2-one ethylene ketal

Product 1

HCID 130796391-[4-(3-Hydroxypropyloxy)phenyl]propan-2-oneYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(4-Hydroxyphenyl)propan-2-one ethylene ketal (3.88 g) was added to a solution of sodium hydroxide (1.5 g) in water (30 ml) and the mixture was stirred at room temperature for 30 minutes. 1-Bromo-3-hydroxypropane (2.98 g) was added and the mixture was boiled under reflux with stirring for 11/2 hours. After cooling water (50 ml) was added, the mixture was extracted with ether, the extracts dried (MgSO4) and evaporated to give the title compound (3.94 g) as its ethylene ketal.

Workup

  1. temperatureunder reflux
  2. stirringwith stirring for 11/2 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ether
  5. dry with materialthe extracts dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f9fb21408b294431a90c83cd983e6cf7
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

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