Water → (E)-methyl 3-methoxy-2-(2-[3-carboxyphenoxy]phenyl)propenoate

HRID 1741875Notes

Reaction equation

HRID 1741875 reaction equation
[CH3:1][O:2]/[CH:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=1)/[C:5]([O:7][CH3:8])=[O:6].[Cr](O)(O)(=O)=[O:25].O>CC(C)=O>[CH3:1][O:2]/[CH:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([OH:25])=[O:23])[CH:17]=1)/[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24425Chromic AcidHCID 15125740HCID 15125740, compound

Product 1

HCID 15125752(E)-methyl 3-methoxy-2-(2-[3-carboxyphenoxy]phenyl)propenoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To (E)-methyl 3-methoxy-2-(2-[3-hydroxymethylphenoxy]phenyl)propenoate (2.43 g, prepared as described in Example 17) stirred in acetone (100 ml) at 5°-10° C., was added chromic acid [made by dissolving chromium trioxide (6.5 g) in 18.5 ml water containing 5.5 ml of concentrated sulphuric acid]until a reddish brown colour persisted, and GC indicated the disappearance of all the starting alcohol. The mixture was then poured into water and extracted with ether. The ether extracts were washed with water, dried and evaporated to give (E)-methyl 3-methoxy-2-(2-[3-carboxyphenoxy]phenyl)propenoate as a pale yellow oil (2.495 g).

Workup

  1. extractionextracted with ether
  2. washThe ether extracts were washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-167926c283b04736ba8cf01a9e7d9654
Source dataset
uspto-grants-1994_08
Patent number
US05334748

Reaction notes

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