4-Hydroxybenzaldehyde → HCID 58097238, compound
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]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
31.2 g (255.4 mmol) of 4-hydroxybenzaldehyde were initially charged in 400 ml of dry DMF, and 105.7 g (766.1 mmol) of potassium carbonate and 50.0 g (332.0 mmol) of (S)-(−)-3-chloro-1,2-propanediol acetonide were added at RT. The mixture was stirred at 160° C. for 16 h. 4000 ml of water were then added, and the mixture was extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases were washed in each case once with 500 ml of water and 500 ml of saturated aqueous sodium chloride solution. After drying over magnesium sulfate, the solvent was removed on a rotary evaporator and the residue was purified by column chromatography on silica gel 60 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8).
Workup
- extractionthe mixture was extracted three times with in each case 500 ml of ethyl acetate
- washThe combined organic phases were washed in each case once with 500 ml of water and 500 ml of saturated aqueous sodium chloride solution
- dry with materialAfter drying over magnesium sulfate
- customthe solvent was removed on a rotary evaporator
- customthe residue was purified by column chromatography on silica gel 60 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8)
Sources & evidence
- ORD record
- ord-024d762e3b39433abee8b46557289a93
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609686B2
Reaction notes
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