4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

HRID 1782714Notes

Reaction equation

HRID 1782714 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.O>[C:13]1([CH2:12][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7498Benzyl BromideHCID 14798Sodium Hydroxide

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 36.6 g (0.3 mol) of 4-hydroxybenzaldehyde in 100 ml of ethanol were added dropwise, one after another, a solution of 12.0 g (0.3 mol) of sodium hydroxide in 100 ml of water and a solution of 36.5 ml of (0.307 mol) of benzylbromide in 100 ml of ethanol and the mixture was then kept for 1 hour at 50° C. The ethanol was extensively distilled off, finally in vacuo, the remaining aqueous emulsion was divided between water and ethyl acetate. The ethyl acetate phase was dried over sodium sulphate and evaporated down in vacuo. The residue remaining crystallised on trituration with petroleum ether and was recrystallised from diisopropylether. 48.0 g (75.4% of theory) of colourless crystals of melting point 118-122° C. were obtained.

Workup

  1. distillationThe ethanol was extensively distilled off, finally in vacuo
  2. dry with materialThe ethyl acetate phase was dried over sodium sulphate
  3. customevaporated down in vacuo
  4. customThe residue remaining crystallised on trituration with petroleum ether
  5. customwas recrystallised from diisopropylether
  6. custom48.0 g (75.4% of theory) of colourless crystals of melting point 118-122° C. were obtained

Sources & evidence

ORD record
ord-2695880349cf4662a892b70f0c5fdb03
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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