4-Hydroxybenzyl Alcohol → HCID 54467276, compound

HRID 2183760Notes

Reaction equation

HRID 2183760 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C([O-])([O-])=[O:11].[K+].[K+].[N+:16]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br)([O-:18])=[O:17]>CC(C)=O>[N+:16]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:11])[OH:7])=[CH:4][CH:3]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 11430Potassium CarbonateHCID 77569alpha-Bromo-2-nitrotoluene

Product 1

HCID 54467276HCID 54467276, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Step 1) To a solution of para-hydroxybenzyl alcohol (2.0 g, 16.1 mol; Aldrich) dissolved in dry acetone (15 mL) was added K2CO3 (4.45 g, 32.2 mmol, 2.0 eq.) and ortho-nitrobenzylbromide (3.83 g, 17.7 mmol, 1.1 eq). The mixture was stirred at ambient temperature for 16 hr and then the solution was concentrated in vacuo. The residue was taken up in EtOAc (100 mL) and then the organic layer was washed with H2O (2×30 mL), brine (30 mL) and dried over MgSO4. The product was recrystallized from Et2O/hexanes to give yellow needles (2.0 g, 60%) of para-(ortho-nitrobenzyl)-hydroxybenzyl alcohol. 1H NMR (CDCl3, 400 MHz) d=8.16 (1H, dd, J=8.2, 1.3 Hz), 7.88 (1H, dd, 7.9, 1.0 Hz), 7.68 (1H, dt, J=7.5, 1.2 Hz), 7.51-7.46 (1H, m), 7.32-7.26 (2H, m), 6.98-6.95 (2H, m), 5.48 (2H, s), 4.61 (2H, s); 13C NMR (CDCl3, 100 MHz) d=157.6, 133.9, 128.7, 128.5, 128.2, 124.9, 114.8, 66.8, 64.9;

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. washthe organic layer was washed with H2O (2×30 mL), brine (30 mL)
  3. dry with materialdried over MgSO4
  4. customThe product was recrystallized from Et2O/hexanes

Sources & evidence

ORD record
ord-d1f9aeb11c3342b7a4f1014464b138bf
Source dataset
uspto-grants-2005_05
Patent number
US06900238B1

Reaction notes

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