Benzaldehyde → HCID 12866413, compound

HRID 903961Notes

Reaction equation

HRID 903961 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].C([Li])CCC.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C1COCC1.CCCCCC>[OH:20][CH:13]([CH:3]1[O:4][CH2:5][CH2:6][NH:1][C:2]1=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 669533-MorpholinoneHCID 178418339Butyllithium

Product 1

HCID 12866413HCID 12866413, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-62 °C

Procedure

Under an atmosphere of nitrogen and in a anhydrous apparatus a mixture of 2.02 g of morpholin-3-one in 60 ml of anhydrous THF was stirred. Dropwise addition was made at room temperature of 26.7 ml of 15% butyl lithium in hexane over 45 minutes. After 2.5 hours of stirring at room temperature the whole was cooled to -62° C. and a solution of 2.02 ml of freshly distilled benzaldehyde in 10 ml of anhydrous THF was added, over 45 minutes. The mixture was kept at -62° C. for 3 hours, allowed to rise to room temperature and kept at this temperature for a further 16 hours. A little water was added and the whole was evaporated to dryness. The residue was taken up with a dilute solution of NaHCO3, extracted with ethyl acetate and washed with H2O. The solution was dried over Na2SO4, filtered and evaporated to dryness. The solid residue was ground with 40 ml of ethyl ether and filtered, to obtain 2.4 g of 2-(α-hydroxy-benzyl)-morpholin-3-one which was crystallized from ethyl acetate, melting point 130°-140° C.

Workup

  1. additionDropwise addition
  2. stirringAfter 2.5 hours of stirring at room temperature the whole
  3. customto rise to room temperature
  4. waitkept at this temperature for a further 16 hours
  5. customthe whole was evaporated to dryness
  6. extractionextracted with ethyl acetate
  7. washwashed with H2O
  8. dry with materialThe solution was dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. filtrationfiltered

Sources & evidence

ORD record
ord-a5645eebbbc44c2f950103bd6ad03478
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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