4-Hydroxybenzaldehyde → HCID 59830893, compound

HRID 403012Notes

Reaction equation

HRID 403012 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-].[K+].[K+].[CH2-:16][C:17]([CH3:19])=[O:18].Cl[CH2:21][C@H:22]([OH:25])[CH2:23]O.O>CN(C=O)C>[CH3:16][C:17]1([CH3:19])[O:25][C@@H:22]([CH2:23][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:21][O:18]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 178521078HCID 178521078, compound

Product 1

HCID 59830893HCID 59830893, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

An amount of 12.5 g (102.4 mmol) of 4-hydroxybenzaldehyde were introduced under argon in 166 ml of dry DMF and admixed at RT with 42.4 g (307.1 mmol) of potassium carbonate and also 20.05 g (133.1 mmol) of (R)-(−)-3-chloro-1,2-propanediol acetonide. The batch was stirred at 160° C. for 16 hours. The batch was then admixed with water and extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. Following filtration, the solvent was removed on a rotary evaporator and the residue was purified by means of column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:2).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltration
  5. customthe solvent was removed on a rotary evaporator
  6. customthe residue was purified by means of column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:2)

Sources & evidence

ORD record
ord-32902390ab7948c2a7c40dbf67881991
Source dataset
uspto-grants-2014_06
Patent number
US08741834B2

Reaction notes

Loading…