3-Hydroxybenzyl alcohol → 3-(2-Propyn-1-yloxy)benzenemethanol

HRID 16724

Reaction equation

HRID 16724 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[OH-].[Na+].[CH2:12](Br)[C:13]#[CH:14].C1(C)C(C)=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6])[C:13]#[CH:12]

Participants

8

Reactant 5

HCID 1023-Hydroxybenzyl alcoholHCID 311Citric AcidHCID 7237O-XyleneHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 107970673-(2-Propyn-1-yloxy)benzenemethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxybenzylalcohol (2.4 g, 20 mmol) in THF (50 mL) and water (2.5 mL) was first added powdered sodium hydroxide (1.5 g, 37.5 mmol) and then a solution of propargyl bromide, dissolved as an 80% weight solution in xylene (3.36 mL, 30 mmol). The reaction mixture was heated at reflux for 6 h. To the mixture was added 10% citric acid (2.5 mL) and the solvent was removed under vacuum. The residue was extracted with ethyl acetate (3×15 mL) and the combined organic layers were washed with saturated NaCl solution (10 mL), dried over MgSO4 and concentrated to give the 3-propargyloxybenzyl alcohol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. customthe solvent was removed under vacuum
  4. extractionThe residue was extracted with ethyl acetate (3×15 mL)
  5. washthe combined organic layers were washed with saturated NaCl solution (10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4df0e5f14c14062970be199319756ce
Source dataset
uspto-grants-2010_06
Patent number
US07737226B2

Linked notes

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