3-Hydroxybenzaldehyde → HCID 86649162, compound

HRID 1925508Notes

Reaction equation

HRID 1925508 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].FC(F)(F)S(O[CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2)(=O)=O.O>CS(C)=O>[C:19]12([CH2:18][O:1][C:2]3[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=3)[CH:5]=[O:6])[CH2:20][CH:21]3[CH2:27][CH:25]([CH2:24][CH:23]([CH2:22]3)[CH2:28]1)[CH2:26]2

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 11522241HCID 11522241, compound

Product 1

HCID 86649162HCID 86649162, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 3-hydroxybenzaldehyde (0.54 g, 4.42 mmol) in dimethyl sulfoxide (5 mL) was added sodium hydride (60%, 0.186 g) in portions. The mixture was stirred for 10 minutes and then was added a solution of Intermediate 34 (1.32 g, 4.42 mmol) in dimethyl sulfoxide (2 mL). The reaction mixture was stirred at 70° C. for 48 hours and the mixture was poured into water and extracted with ether. The organic layer was washed with a solution of sodium hydroxide 2N, water and brine. The solvent was removed under reduced pressure and the crude was purified by column chromatography with silica gel, eluting by hexane/ethyl acetate (10:1) to give the title compound as an oil (0.493 g, 41%).

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 48 hours
  2. extractionextracted with ether
  3. washThe organic layer was washed with a solution of sodium hydroxide 2N, water and brine
  4. customThe solvent was removed under reduced pressure
  5. customthe crude was purified by column chromatography with silica gel
  6. washeluting by hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-d6f545d1e9a045beb52e7b68cdd3bb7c
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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