Methanol → Methyl 3-hydroxy-5-methoxy-4-nitrophenylacetate

HRID 1357863Notes

Reaction equation

HRID 1357863 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[N+:8]([O-:10])=[O:9].[CH3:17]O>Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 181880853-Hydroxy-5-methoxy4-nitrophenylacetic acid

Product 1

HCID 18188097Methyl 3-hydroxy-5-methoxy-4-nitrophenylacetate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A solution of 3-hydroxy-5-methoxy-4-nitrophenylacetic acid (0.76 g, Reference Example 12) in methanol (100 mL) and concentrated hydrochloric acid (5 drops) was heated at reflux through 3A molecular sieve for 4 hours, then evaporated. The residue was partitioned between ethyl acetate and water. The organic phase was washed with water, then with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with dichloromethane, then with a mixture of methanol and dichloromethane (1:49, v/v) to give the title compound (0.34 g).

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. dry with materialwith brine, then dried
  5. customevaporated
  6. additionwith a mixture of methanol and dichloromethane (1:49, v/v)

Sources & evidence

ORD record
ord-6d09f92e665342db921d83f9643a269b
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

Loading…