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

HRID 499015Notes

Reaction equation

HRID 499015 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-6480b9e28b8f42b7aca5f8c8104d0924
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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