Benzyl Bromide → Benzyl 2-benzyloxy-5-formylbenzoate

HRID 1623716Notes

Reaction equation

HRID 1623716 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:15]([C:17]1[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([CH:25]=1)[C:22]([OH:24])=[O:23])=[O:16]>CN(C)C=O>[CH3:11][CH2:10][CH2:9][CH:8]([CH3:13])[CH3:7].[C:22]([O:24][CH2:13][CH3:8])(=[O:23])[CH3:21].[CH:15]([C:17]1[CH:18]=[CH:19][C:20]([O:26][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:21]([CH:25]=1)[C:22]([O:24][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:23])=[O:16]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 692265-Formylsalicylic acid

Product 2

HCID 10405334Benzyl 2-benzyloxy-5-formylbenzoateHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (14.71 g, 45.1 mmol) and benzyl bromide (4.47 ml, 37.6 mmol) were added dropwise to a solution of 5-formyl-2-hydroxybenzoic acid (2.5 g, 15.05 mmol) in dimethylformamide (40 ml). The mixture was stirred for 24 hours. The dimethylformamide was removed in vacuo and the residue was redissolved in ethyl acetate (150 ml), washed with water (3×30 ml), dried (MgSO4) and the solvent removed in vacuo to give a off white solid. Trituration with 6:1 isohexane/ethyl acetate yielded the title compound as a white solid. 4.20 g.

Workup

  1. customThe dimethylformamide was removed in vacuo
  2. dissolutionthe residue was redissolved in ethyl acetate (150 ml)
  3. washwashed with water (3×30 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a off white solid

Sources & evidence

ORD record
ord-e38338800ebd4c66b4a4999cc290894e
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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