Ammonia → (4-Hydroxyphenyl)acetamide

HRID 341715Notes

Reaction equation

HRID 341715 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C)=O)=[CH:4][CH:3]=1.[NH3:13]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:13])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 86986(4-Hydroxyphenyl)acetamide

Procedure

Methyl 4-Hydroxyphenylacetate (4) (0.83 g) was dissolved in saturated methanolic ammonia (30 ml) and placed in a thick walled tube with Teflon screw cap. The solution was stirred in this sealed tube at room temperature for 72 hours. Reaction mixture was concentrated and redissolved in methanol-chloroform (2:8 volume by volume, 75 ml). No crystallization occurred so the solution was concentrated to half its volume and hexane was added with heating. Cooling to 0° C. gave crystals of 4-Hydroxyphenylacetamide (13) (0.524 g). This was confirmed by spectroscopy--1H NMR (d6DMSO+CF3CO2D) δ 3.23 (s, 2 H), 6.63 (d, 2 H), 7.00 (d, 2 H).

Workup

  1. customscrew cap
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutionredissolved in methanol-chloroform (2:8 volume by volume, 75 ml)
  5. customNo crystallization
  6. concentrationwas concentrated to half its volume and hexane
  7. additionwas added
  8. temperaturewith heating
  9. temperatureCooling to 0° C.

Sources & evidence

ORD record
ord-2ad2afa3a63145b1847a0d4e91b9e8c9
Source dataset
uspto-grants-1999_01
Patent number
US05855885

Reaction notes

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