M-Cresol → 3-(3-Methylphenoxy)propan-1-ol

HRID 2220172Notes

Reaction equation

HRID 2220172 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][CH2:11][CH2:12][OH:13].[OH-].[Na+]>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 3

HCID 342M-CresolHCID 123133-Chloro-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 122931893-(3-Methylphenoxy)propan-1-olYield 87.2%

Procedure

A stirred solution of 25 grams (0.23 mole) of 3-methylphenol and 18.8 grams (0.20 mole) of 3-chloropropan-1-ol in 100 mL of aqueous 10% sodium hydroxide was heated at reflux for about 40 minutes. After this time, the reaction mixture was cooled to ambient temperature and extracted with three 100 mL portions of diethyl ether. The combined extracts were then washed with three 50 mL portions of an aqueous dilute sodium hydroxide solution and dried with sodium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure, yielding 29 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 40 minutes
  2. extractionextracted with three 100 mL portions of diethyl ether
  3. washThe combined extracts were then washed with three 50 mL portions of an aqueous dilute sodium hydroxide solution
  4. dry with materialdried with sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f73a805cf7fb4a0583804d92ef5123d3
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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