Benzyl Bromide → Benzyl 2-benzyloxy-5-formylbenzoate

HRID 1583023Notes

Reaction equation

HRID 1583023 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([C:11]1[CH:19]=[C:15]([C:16]([OH:18])=[O:17])[C:14]([OH:20])=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:20][C:14]1[CH:13]=[CH:12][C:11]([CH:9]=[O:10])=[CH:19][C:15]=1[C:16]([O:18][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 692265-Formylsalicylic acid

Product 1

HCID 10405334Benzyl 2-benzyloxy-5-formylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (25.6 mL, 0.22 mol, 2.5 eq) was added dropwise to a stirred solution of 5-formylsalicylic acid (10 g, 0.06 mol, 1 eq) and cesium carbonate (84.2 g, 0.26 mol, 3 eq) in N,N-dimethylformamide (150 mL). The reaction mixture was stirred for 3 days and concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL) and the organic solution washed with water (200 mL) and brine (4×200 mL), then dried over sodium sulfate and evaporated in vacuo. This gave a gummy solid which was recrystallized from ethyl acetate and petroleum ether to give a cream coloured powder (16.1 g, 77%). RF (petroleum ether:ethyl acetate 1:1) 0.73. 1H NMR (CDCl3) δ9.91 (s, 1H, O═C—H), 5.38 (s, 2H, CH2Ph), 5.28 (s, 2H, CH2Ph).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  3. washthe organic solution washed with water (200 mL) and brine (4×200 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThis gave a gummy solid which
  7. customwas recrystallized from ethyl acetate and petroleum ether
  8. customto give a cream

Sources & evidence

ORD record
ord-04b8330a7e044a2e9474bd53b5577c5a
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

Loading…