O-ethylhydroxylamine hydrochloride → Methyl 3-(ethoxyimino)-3-(4-hydroxyphenyl)propanoate

HRID 2243865Notes

Reaction equation

HRID 2243865 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH2:15]([O:17][NH2:18])[CH3:16].Cl>CO>[CH2:15]([O:17][N:18]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH3:16]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 508465Methyl (4-Hydroxybenzoyl)acetate

Product 1

HCID 136360155Methyl 3-(ethoxyimino)-3-(4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 3-(4-hydroxyphenyl)-3-oxopropanoate (1 g) and EtONH2.HCl (600 mg) in methanol (10 mL) was heated at 65° C. for 2 h. Methanol was removed in vacuo, and saturated sodium bicarbonate was added to the residue. The aqueous solution was extracted with ethyl acetate (×4), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound as a colorless oil, which was used directly in Step B. HPLC retention time: 1.51 min (method A). MS (ESI) (M+H)+ 238.09.

Workup

  1. customMethanol was removed in vacuo, and saturated sodium bicarbonate
  2. additionwas added to the residue
  3. extractionThe aqueous solution was extracted with ethyl acetate (×4)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-eae2bdb5120142908ee0b7a010a7220e
Source dataset
uspto-grants-2010_03
Patent number
US07678784B2

Reaction notes

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