Hydrochloric Acid → 4-(Acetyloxy)-3-nitrobenzoic acid

HRID 2273452Notes

Reaction equation

HRID 2273452 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22].Cl>CC(C)=O.ClCCl>[C:21]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])(=[O:23])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 120334-Hydroxy-3-nitrobenzoic acid

Product 1

HCID 140573074-(Acetyloxy)-3-nitrobenzoic acidYield 51.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Hydroxy-3-nitro-benzoic acid (5.49 g, 30 mmol) was dissolved in acetone (10 ml), triethylamine (10 ml) and acetic acid anhydride (5.67 ml, 60 mmol). The solution was stirred for 24 h at rt. The reaction mixture was added dichloromethane (100 ml), ice (20 g) and acidified by addition of concentrated hydrochloric acid. The aqueous phase was extracted with dichloromethane (2×25 ml). The combined organic phases were stirred with sodium sulphate added activated carbon, filtered and evaporated. Recrystallisation from EtoAc:Heptane gave 3.45 g (51%) pure material.

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane (2×25 ml)
  2. stirringThe combined organic phases were stirred with sodium sulphate added activated carbon
  3. filtrationfiltered
  4. customevaporated
  5. customRecrystallisation from EtoAc

Sources & evidence

ORD record
ord-88c87c053537499ea67b6ff09a826701
Source dataset
uspto-grants-2015_09
Patent number
US09121110B2

Reaction notes

Loading…