Water → HCID 57582490, compound

HRID 526022Notes

Reaction equation

HRID 526022 reaction equation
[O-]CC.[Na+].[OH:5][C:6](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)[C:7]([OH:9])=[O:8].[BH4-].[Na+].O>CO.CCCCCCC.C(OCC)(=O)C>[OH:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

8

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 4311764Sodium borohydrideHCID 66905811HCID 66905811, compound

Product 1

HCID 57582490HCID 57582490, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
7.5 °C

Procedure

Sodium ethoxide (1.8 g, 26.4 mmol) was added portionwise at 0° C. to a stirred solution of 2-hydroxy-3-(3-nitrophenyl)acrylic acid (5.25 g, 25.0 mmol) in methanol (131 ml) to form a clear, pale yellow solution. Sodium borohydride (1 g, 26.4 mmol) was then carefully added in two portions and the mixture stirred at 5-10° C. for 30 mins. A small amount of water was then added to quench the reaction and destroy any excess NaBH4. The methanol was removed in vacuo to give a solid residue, which was ground with a 5:2 mixture of ethyl acetate and heptane (21 ml) then further ground with 3% aqueous methanol. The resulting solid was collected by filtration and dried in vacuo to give 2-hydroxy-3-(3-nitrophenyl)propionic acid (3.0 g, 57%).

Workup

  1. customto form a clear, pale yellow solution
  2. customto quench
  3. customthe reaction
  4. customdestroy any excess NaBH4
  5. customThe methanol was removed in vacuo
  6. customto give a solid residue, which
  7. filtrationThe resulting solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-3c0a5c9ee37b49aca81a5a192d92d883
Source dataset
uspto-grants-2016_05
Patent number
US09345680B2

Reaction notes

Loading…