Sodium Hydroxide → HCID 118292793, compound

HRID 1486841Notes

Reaction equation

HRID 1486841 reaction equation
Cl[O-].[Na+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14](/[CH:18]=[N:19]/[OH:20])[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:21]=[C:22]([CH2:27][C:28]([O:30]C)=[O:29])[C:23]([O:25]C)=[O:24].[OH-].[Na+]>C1COCC1.CO>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([C:18]2[CH2:21][C:22]([CH2:27][C:28]([OH:30])=[O:29])([C:23]([OH:25])=[O:24])[O:20][N:19]=2)[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 69240Dimethyl itaconateHCID 5331739HCID 5331739, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 118292793HCID 118292793, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous sodium hypochlorite solution (5%, 1081 g) was added dropwise to a solution of (E)-1-(3-(benzyloxy)phenyl)-N-hydroxymethanimine (150 g) and dimethyl 2-methylenesuccinate (104 g) in THF (1500 mL) at 5 C (internal temperature: 30 C or lower) over 1 hour, and then, the obtained mixture was stirred at 5 C for 1 hour. To the reaction mixture, methanol (750 mL) was added, and then, a 2 M aqueous sodium hydroxide solution (750 mL) was added dropwise at 5 C (internal temperature: 20 C or lower) over 40 minutes. The obtained mixture was gradually warmed to room temperature and stirred overnight at room temperature. The reaction mixture was concentrated into half the volume under reduced pressure, and then, water (5000 mL) and ethyl acetate (1500 mL) were added to the residue. The aqueous layer was washed with ethyl acetate (1500 mL), then 6 M hydrochloric acid (250 mL) was added thereto, and the obtained mixture was subjected to extraction with ethyl acetate (1500 mL×2). The extract was washed with brine (1500 mL) and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was washed with diethyl ether (10 mL) and hexane (1000 mL) to obtain the title compound (217 g).

Workup

  1. stirringstirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated into half the volume under reduced pressure
  3. additionwater (5000 mL) and ethyl acetate (1500 mL) were added to the residue
  4. washThe aqueous layer was washed with ethyl acetate (1500 mL)
  5. addition6 M hydrochloric acid (250 mL) was added
  6. extractionthe obtained mixture was subjected to extraction with ethyl acetate (1500 mL×2)
  7. washThe extract was washed with brine (1500 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. washThe residue was washed with diethyl ether (10 mL) and hexane (1000 mL)

Sources & evidence

ORD record
ord-550527b356a64d979fef58c3b3110867
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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