Hydrochloric Acid → 3-(4-Methoxyphenoxy)propanol

HRID 2108115Notes

Reaction equation

HRID 2108115 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][CH2:13][OH:14].[OH-].[Na+].Cl>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][CH2:13][OH:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 90154-MethoxyphenolHCID 123083-Bromo-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 3029623-(4-Methoxyphenoxy)propanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-methoxyphenol (1.24 g) and 3-bromopropanol (1.18 ml) in DMSO (15 ml) was added in one portion powdered sodium hydroxide (1.12 g). The mixture was stirred for 0.75 h then poured into 2N hydrochloric acid (100 ml) and extracted with ethyl acetate (100 ml). The organic phase was washed with water (100 ml), dried and concentrated to give the title compound (1.785 g) as a pale brown solid, m.p. 56°-60°.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic phase was washed with water (100 ml)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-376dcd59bef1460b8a7820bf6461aaa1
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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