Hydrochloric Acid → Ethyl 4-hydroxyphenylglycine, hydrochloride

HRID 862006Notes

Reaction equation

HRID 862006 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[ClH:13].[CH3:14][CH2:15]O>>[ClH:13].[CH2:14]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:9][C:10]([OH:12])=[O:11])[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67149N-(4-Hydroxyphenyl)glycine

Product 1

HCID 131720465Ethyl 4-hydroxyphenylglycine, hydrochlorideYield 70%

Procedure

To a suspension of 4-hydroxyphenylglycine (18.00 g, 0.11 mol) in EtOH (100 mL) was added 20% ethanolic HCl (30 mL). The mixture was heated at reflux for 14 h, then was allowed to cool and was concentrated under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, and the organic extract was concentrated in vacuo to afford the tide compound (15.00 g, 70%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 14 h
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  6. extractionthe organic extract
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-bc0ddc97db504d6c971baaf5886f4135
Source dataset
uspto-grants-1998_02
Patent number
US05716972

Reaction notes

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