Acetic Anhydride → HCID 71281758, compound

HRID 1481686Notes

Reaction equation

HRID 1481686 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:4][C:3]=1[OH:13].[CH3:14][C:15](OC(C)=O)=[O:16]>C(Cl)(Cl)Cl>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15](=[O:16])[CH3:14])=[C:3]([OH:13])[CH:4]=1)(=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 30788751-Butanone, 1-(4-amino-3-hydroxyphenyl)-

Product 1

HCID 71281758HCID 71281758, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(4-amino-3-hydroxyphenyl)butan-1-one (0.71 g, 4.0 mmol) in CHCl3 (8 mL) was added Ac2O (0.4 mL, 4.2 mmol, 1.06 eq) at 0° C. After 5 min, reaction was quenched with H2O then extracted with CH2Cl2 (3×30 mL). Solvent was removed under reduced pressure to afford N-(4-butyryl-2-hydroxyphenyl)acetamide (0.81 g, 3.7 mmol, 93%) with ca. 80% purity which was used in the next step without further purification.

Workup

  1. customreaction
  2. customwas quenched with H2O
  3. extractionthen extracted with CH2Cl2 (3×30 mL)
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9792dbe2ddf84455a93ab336e3c7f95d
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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