3-Bromo-1-propanol → 3-[3-(Pentyloxy)phenoxy]propanol

HRID 439753Notes

Reaction equation

HRID 439753 reaction equation
[H-].[Na+].[CH2:3]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:17][CH2:18][CH2:19][OH:20]>CN(C)C=O>[CH2:3]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:17][CH2:18][CH2:19][OH:20])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 156922293-(Pentyloxy)phenol

Product 1

HCID 224080143-[3-(Pentyloxy)phenoxy]propanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 0.80 g of 60% NaH in 28 ml of anhydrous dimethylformamide is cooled in an ice bath. To this is added 3.01 g of the above 3-pentyloxyphenol oil dissolved in 7 ml of anhydrous dimethylformamide. This mixture is then stirred at room temperature for 45 minutes; 1.81 ml of 3-Bromopropanol are added; and the resultant mixture is stirred at 60° C. for 17 hours. The solvent is removed under vacuum, and the residue worked up in same manner as above. The residue obtained is flash chromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane:ether to yield 3-[3-(pentyloxy)phenoxy]propanol as a pale yellow oil.

Workup

  1. temperatureis cooled in an ice bath
  2. customThe solvent is removed under vacuum
  3. customThe residue obtained
  4. customchromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane

Sources & evidence

ORD record
ord-953d1a9f5ed04b66a2fcdd26a50d1535
Source dataset
uspto-grants-1996_05
Patent number
US05516767

Reaction notes

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