Methanol → HCID 19611296, compound

HRID 1602488Notes

Reaction equation

HRID 1602488 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, compoundYield 94%

Procedure

With cooling at -30° C. or below, thionyl chloride (75 ml) was added dropwise to methanol (150 ml). At -30° C., 3-(4-hydroxy-3-nitrophenyl)propionic acid (26.20 g, 0.12 mol) was added to this solution. The reaction solution was stirred at room temperature for 1 hour and then at 40 to 50° C. for 3 hours. The reaction solution was concentrated under reduced pressure. Then, a procedure of adding toluene (100 ml) to the residue and concentrating the mixture under reduced pressure was repeated twice. Thereafter, the resulting residue was crystallized from ether-hexane to give methyl 3-(4-hydroxy-3-nitrophenyl)propionate (26.20 g, 94%).

Workup

  1. temperatureWith cooling at -30° C. or below
  2. waitat 40 to 50° C. for 3 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. concentrationThen, a procedure of adding toluene (100 ml) to the residue and concentrating the mixture under reduced pressure
  5. customThereafter, the resulting residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-1d539c140a524645abadb601bb463b56
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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