Hydrochloric Acid → (3-Formyl-4-methoxy-phenyl)-acetic acid

HRID 553296

Reaction equation

HRID 553296 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[OH2:16]>O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O>[CH:2]([C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 671652482-(3-(Bromomethyl)-4-methoxyphenyl)acetic acid

Product 1

HCID 23025459(3-Formyl-4-methoxy-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 9837674Copper(II) nitrate trihydrateCatalyst

Procedure

Copper(II) nitrate trihydrate (3.3 g) was added to (3-bromomethyl-4-methoxy-phenyl)-acetic acid (1.4 g) in water (50 mL) and heated to reflux for 75 minutes. On cooling the reaction mixture was acidified with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was separated and washed sequentially with 2M aqueous hydrochloric acid (2×50 mL), brine (50 mL), dried (magnesium sulfate) and concentrated. Purification on silica, eluting iso-hexane/ethyl acetate [4:1 to 1:1 to 0:1], to give the subtitle compound as a solid (0.26 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 75 minutes
  3. temperatureOn cooling the reaction mixture
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was separated
  6. washwashed sequentially with 2M aqueous hydrochloric acid (2×50 mL), brine (50 mL)
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated
  9. customPurification on silica
  10. washeluting iso-hexane/ethyl acetate [4:1 to 1:1 to 0:1]

Sources & evidence

ORD record
ord-d64a7e1c21a944a5aa6d25d2cf1665e1
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Linked notes

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