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
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
An amount of 31.2 g (255.4 mmol) of 4-hydroxybenzaldehyde was introduced in 400 ml of dry DMF and admixed at RT with 105.7 g (766.1 mmol) of potassium carbonate and also 50.0 g (332.0 mmol) of (S)-(−)-3-chloro-1,2-propanediol acetonide. The batch was stirred at 160° C. for 16 hours. The batch was then admixed with 4000 ml of water and extracted with three times 500 ml of ethyl acetate. The combined organic phases were washed once each 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 (eluent gradient: ethyl acetate/petroleum ether 1:9→2:8).
Workup
- extractionextracted with three times 500 ml of ethyl acetate
- washThe combined organic phases were washed once each 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 (eluent gradient: ethyl acetate/petroleum ether 1:9→2:8)
Sources & evidence
- ORD record
- ord-1108c9725b7c43dab7c405ed6eed5949
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741834B2
Reaction notes
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