Hydrochloric Acid → 4-Benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid

HRID 1695998Notes

Reaction equation

HRID 1695998 reaction equation
[CH2:1]([N:8]1[C:13]([CH2:15][OH:16])([CH3:14])[CH2:12][O:11][CH2:10][C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].[Br-].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+].Cl.[O-:35]Cl=O.[Na+]>O>[CH2:1]([N:8]1[C:9](=[O:17])[CH2:10][O:11][CH2:12][C:13]1([CH3:14])[C:15]([OH:35])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 253877Potassium BromideHCID 2724126TempoHCID 223427394-Benzyl-5-(hydroxymethyl)-5-methylmorpholin-3-oneHCID 23665760Sodium HypochloriteHCID 23668197Sodium Chlorite

Product 1

HCID 672692114-Benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Combine 4-benzyl-5-(hydroxymethyl)-5-methylmorpholin-3-one (11.75 g, 0.05 mol) ethyl acetate (75 ml), and KBr in water (0.5 M, 10 ml), followed by addition of 2,2,6,6-tetramethylpiperidine-1-oxyl (0.16 g, 1 mmol). Add solution of 12% NaClO in water (39 g, 62.5 mmol) dropwise to the mixture over 30 minutes at 5° C. at pH of 8.0-10.0. After 30 minutes, adjust the pH to 5.0 by addition of 35% hydrochloric acid, followed by addition of 25% NaClO2 in water (22.7 g, 62.5 mmol) over 30 minutes. Stirring continues for 3 hours at ambient temperature. Recover the product by extraction with ethyl acetate, washed with brine, to give 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid.

Workup

  1. waitcontinues for 3 hours at ambient temperature
  2. customRecover the product
  3. extractionby extraction with ethyl acetate
  4. washwashed with brine

Sources & evidence

ORD record
ord-dab02b06c15f4a7992e97eb5c548937b
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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