4-Hydroxybenzaldehyde → HCID 59830893, compound

HRID 2362811Notes

Reaction equation

HRID 2362811 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+].Cl[CH2:17][C@H:18]1[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]1>CN(C=O)C>[CH3:23][C:20]1([CH3:24])[O:19][C@@H:18]([CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:22][O:21]1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 59830893HCID 59830893, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1.79 g (14.6 mmol) of p-hydroxybenzaldehyde are dissolved in absolute DMF (10 ml), and 14.2 g (102.5 mmol) of potassium carbonate and 3.3 g (22.0 mmol) of (R)-(+)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane are added. The mixture is heated at 150° C. for 24 h. The mixture is then concentrated using a rotary evaporator, and the residue is partitioned between dichloromethane and water. The combined organic phases are extracted with dichloromethane (three times, 20 ml each), washed with sat. sodium chloride solution and dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5:1).

Workup

  1. concentrationThe mixture is then concentrated
  2. customa rotary evaporator
  3. customthe residue is partitioned between dichloromethane and water
  4. extractionThe combined organic phases are extracted with dichloromethane (three times, 20 ml each)
  5. washwashed with sat. sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customAfter removal of the solvent
  8. customon a rotary evaporator
  9. customthe crude product is purified chromatographically on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-58af7fb87c974f8a85757e6bc374e68e
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

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