Hydrochloric Acid → (3-Acetoxy-4-nitro-phenyl)acetic acid

HRID 49714Notes

Reaction equation

HRID 49714 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[OH-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>C(OCC)C>[C:17]([O:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 235083252-(3-Hydroxy-4-nitrophenyl)acetic acid

Product 1

HCID 17946639(3-Acetoxy-4-nitro-phenyl)acetic acidYield 519.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of (3-hydroxy-4-nitro-phenyl)acetic acid (1 2.0 g), aqueous sodium hydroxide (152.3 mL, 1M) and diethyl ether (150 mL), cooled to 0° C. in an ice salt bath, was treated dropwise with acetic anhydride (8.1 g) at a rate to maintain the temperature at 0° C. When the addition was complete the mixture was stirred at 0° C. for a further 2 hours then acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The extracts were dried over magnesium sulphate and then evaporated to give the title compound (12.6 g) as an oil.

Workup

  1. temperatureto maintain the temperature at 0° C
  2. additionWhen the addition
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-60d046c6b3554acfb33ad147ac87161e
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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