Hydrochloric Acid → 3-Benzyloxy-5-methoxy-4-nitrophenol

HRID 2305625Notes

Reaction equation

HRID 2305625 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:18]([O-:20])=[O:19])=[C:11]([O:16][CH3:17])[CH:12]=[C:13](F)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=[O:23].[OH-].[Na+].Cl>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([OH:23])[CH:12]=[C:11]([O:16][CH3:17])[C:10]=1[N+:18]([O-:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 18433397Benzyl 5-fluoro-3-methoxy-2-nitrophenyl ether

Product 1

HCID 184333963-Benzyloxy-5-methoxy-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-benzyloxy-5-fluoro-2-nitroanisole(0.75 g), dimethylsulphoxide(5 mL) and 5N aqueous sodium hydroxide(2 mL) was stirred at 70° C. for 3 h. The mixture was diluted with water and acidified with concentrated hydrochloric acid, extracted with ethyl acetate and the extract was washed with water dried and evaporated to dryness to give the product (0.71 g), (m/e274, MH−).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with water
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-f8c7bd2909f44732920f04a57e0e0e42
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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