4-Hydroxybenzyl Alcohol → 4-(3-Chloropropoxy)benzyl alcohol

HRID 365590Notes

Reaction equation

HRID 365590 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.Br[CH:11]([Cl:14])[CH2:12][CH3:13].[OH-].[K+]>C(O)C>[Cl:14][CH2:11][CH2:12][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 14797Potassium HydroxideHCID 36872Propane, bromochloro-

Product 1

HCID 228974964-(3-Chloropropoxy)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-hydroxy benzyl alcohol CAS NO. [623-05-2] (10 g, 80.5 mmol) in ethanol (70 mL) was treated with 1, 3 bromochloro propane (16.0 g, 100 mmol) and potassium hydroxide (5.0 g, 89 mmol) was refluxed for 2 hours. The solution was cooled and filtered and then the filtrate concentrated. The concentrate was taken up in ether and washed with water, brine and dried over magnesium sulfate. The material was chromatographed on silica gel using ethyl acetate/hexanes (3:7) to yield 11.6 g of the product as a white solid: Mp=65° C.; 1H NMR (DMSO) 7.21 (d, 2 H, J=8.8 Hz), 6.88 (d, 2 H, J=8.8 Hz), 5.03 (t, 1 H, J=5.7 Hz), 4.40 (d, 2H, J=5.5 Hz), 4.05 (t, 2 H, J=6.1 Hz), 3.77 (t, 2 H, J=6.4 Hz); MS eI m/z 200.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe solution was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe material was chromatographed on silica gel

Sources & evidence

ORD record
ord-617a1112a08740ad8755df235afb40b6
Source dataset
uspto-grants-2000_10
Patent number
US06127404

Reaction notes

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