4-Hydroxybenzaldehyde → methyl 4-[(4-formylphenoxy)methyl]benzoate

HRID 1497981Notes

Reaction equation

HRID 1497981 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:16][O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:18]([O:17][CH3:16])=[O:27])=[CH:20][CH:21]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 877931methyl 4-[(4-formylphenoxy)methyl]benzoateYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxybenzaldehyde (244.2 mg, 2 mmol) and cesium carbonate (445 mg, 1.36 mmol) in anhydrous DMF (8 mL) was added methyl-4-(bromomethyl)benzoate (481 mg, 2.1 mmol). The resulting mixture was stirred for 24 hours at room temperature, after which time the mixture was concentrated under reduced pressure. The resulting crude was partitioned between dichloromethane (30 mL) and water (10 mL). The mixture was filtered through a phase separator, washed with dichloromethane and the solvent was removed in vacuo to yield the title compound as an off-white solid (520 mg, 96%).

Workup

  1. concentrationafter which time the mixture was concentrated under reduced pressure
  2. customThe resulting crude was partitioned between dichloromethane (30 mL) and water (10 mL)
  3. filtrationThe mixture was filtered through a phase separator
  4. washwashed with dichloromethane
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c141712ef471417ca2bf4739ec75665d
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

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