Benzyl Bromide → 4-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

HRID 929099Notes

Reaction equation

HRID 929099 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].O1CCOCC1>O>[CH2:12]([O:11][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[C:9]=1[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 312751,4-DioxaneHCID 803952,4-Dihydroxy-3-methylbenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 597616904-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 2,4-dihydroxy-3-methyl-benzaldehyde (3.31 g, 21.8 mmol), benzylbromide (4.09 g, 23.9 mmol), NaHCO3 (5.49 g, 65.4 mmol), 1,4-dioxane (30 mL) and water (12 mL) was stirred at 60° C. for overnight. Then the reaction mixture was cooled to RT, water (100 mL) was added, extracted with EtOAc (2×200 mL). The extract was dried over Na2SO4, evaporated. The residue was purified on SiO2 (25 g) column, hexane-EtOAc (0 to 5%). Yield 1.57 g (6.48 mmol, 29%) as off-white solid.

Workup

  1. temperatureThen the reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (2×200 mL)
  3. dry with materialThe extract was dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified on SiO2 (25 g) column, hexane-EtOAc (0 to 5%)

Sources & evidence

ORD record
ord-a8fd48b6f130494485a286b6f1355493
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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