3-Hydroxybenzaldehyde → 3-Benzyloxybenzaldehyde

HRID 710382Notes

Reaction equation

HRID 710382 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 743423-BenzyloxybenzaldehydeYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of benzyl bromide (1.4 g; 8.2 mmol), 3-hydroxybenzaldehyde (1.0 g; 8.2 mmol) and Cs2CO3 (2.67 g; 8.2 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature under N2. After evaporation of solvent in vacuo, the residue was diluted to 20 ml with CH2Cl2, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (1.33 g; 76%) as creamy foam. 1H-NMR (CDCl3) 5.11 (s, 2H); 7.2-7.48 (m, 9H); 9.96 (s, 1H).

Workup

  1. customAfter evaporation of solvent in vacuo
  2. additionthe residue was diluted to 20 ml with CH2Cl2
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness

Sources & evidence

ORD record
ord-b0fc5e05417e43f7a6d17d1df81df3c2
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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