Ammonia → methyl (E)-beta-methoxy-2-(3-methylphenoxy)cinnamate

HRID 1899791Notes

Reaction equation

HRID 1899791 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.[H-].[Na+].S(OC)(O[CH3:28])(=O)=O.N>CN(C)P(=O)(N(C)C)N(C)C.O>[CH3:28][O:20]/[C:5](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)=[CH:4]/[C:3]([O:2][CH3:1])=[O:21]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 54054832HCID 54054832, compound

Product 1

HCID 86749649methyl (E)-beta-methoxy-2-(3-methylphenoxy)cinnamateYield 22.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 5 g (18 mmol) of methyl2-(3-methylphenoxy)benzoylacetate in 30 ml of hexamethylphosphoric triamide (HMPT) is added dropwise to a suspension of 500 mg (21 mmol) of sodium hydride in 20 ml of HMPT, and the mixture is stirred until evolution of gas ceases. Then 2.5 g (20 mmol) of dimethyl sulfate are added dropwise, the mixture is stirred for 30 min, and then 30 ml of concentrated ammonia solution are added. The mixture is poured into water and extracted with MTB ether. The organic phase is dried and concentrated. Chromatography of the residue on silica gel with hexane/MTB ether yields in the first fractions 1.2 g (22%) of methyl (E)-β-methoxy-2-(3-methylphenoxy)cinnamate (trans product) as yellow oil.

Workup

  1. stirringthe mixture is stirred for 30 min
  2. extractionextracted with MTB ether
  3. customThe organic phase is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fd9de40e9bc54c998988fb966af00488
Source dataset
uspto-grants-1996_11
Patent number
US05573999

Reaction notes

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