Methanol → HCID 19611296, compound

HRID 1766010Notes

Reaction equation

HRID 1766010 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18].[CH3:20]O>>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:20])=[O:15])=[CH:8][C:7]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27741863-(4-hydroxy-3-nitrophenyl)propanoic acid

Product 1

HCID 19611296HCID 19611296, compound

Procedure

Thionyl chloride (15 ml) was added dropwise to a solution of 3-(4-hydroxy-3-nitrophenyl)propionic acid (49 g, 232 mmol) obtained in 1) above in methanol (500 ml), and the mixture was stirred overnight at room temperature. After, the reaction solution was concentrated, water (500 ml) was added to the reaction solution which was then extracted with ethyl acetate. The extract was washed with water and aqueous saturated sodium bicarbonate, dried over magnesium sulfate and concentrated, whereby methyl 3-(4-hydroxy-3-nitrophenyl)propionate (47 g) was obtained as powder.

Workup

  1. concentrationAfter, the reaction solution was concentrated
  2. additionwater (500 ml) was added to the reaction solution which
  3. extractionwas then extracted with ethyl acetate
  4. washThe extract was washed with water and aqueous saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-62bac0fb377342b9a16dbdfa9b5a398f
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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