Potassium Carbonate → HCID 53638351, compound

HRID 1584881Notes

Reaction equation

HRID 1584881 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].C1(C)C=CC(S(O[CH2:21][C@@H:22]2[O:24][CH2:23]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:21][C@@H:22]2[O:24][CH2:23]2)[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 5283932-Chloro-6-hydroxybenzaldehyde

Product 1

HCID 53638351HCID 53638351, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-6-hydroxybenzaldehyde (4.4 g), (R)-glycidyl 4-toluenesulphonate (5.0 g) and potassium carbonate (3.9 g) in dimethylformamide (120 ml) was stirred and heated at 60° C. for 5 hours and allowed to cool over 18 hours. The solvent was removed in vacuo, water (60 ml) was added to the residue and the mixture extracted with ether (3×100 ml). The combined extracts were dried over magnesium sulphate and the solvent was evaporated. The residual oil was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and dichloromethane, followed by neat dichloromethane then a 19:1 mixture of dichloromethane and industrial methylated spirit. Appropriate fractions were combined and the solvent removed in vacuo to give (R)-2-chloro-6-(2,3-epoxypropoxy)benzaldehyde as a pale yellow solid (2.8 g). Other, incompletely purified, fractions gave material which was subjected to repeat chromatography, providing a second crop of product (0.5 g).

Workup

  1. temperatureto cool over 18 hours
  2. customThe solvent was removed in vacuo, water (60 ml)
  3. additionwas added to the residue
  4. extractionthe mixture extracted with ether (3×100 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulphate
  6. customthe solvent was evaporated
  7. customThe residual oil was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and dichloromethane
  8. additiona 19:1 mixture of dichloromethane and industrial methylated spirit
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-63ae14265f604b34a988028753993b73
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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