Ethanol → HCID 70290887, compound

HRID 2287659Notes

Reaction equation

HRID 2287659 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:18])[CH:16]=[CH2:17].[C:19]([O-])([O-])=[O:20].[K+].[K+].[CH2:25]([OH:27])[CH3:26]>>[CH3:13][O:14][C:15](=[O:18])/[C:16](/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:12]=[CH:26][CH2:25][OH:27])=[CH:17]/[O:20][CH3:19]

Participants

5

Reactant 4

HCID 702EthanolHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 70290887HCID 70290887, compoundYield 93%

Procedure

At 24°, toluene-4-sulfonic acid monohydrate (1.11 g, 0.4 mmol) was added to a solution of (E)-3-methoxy-2-[(E)-2-[(R)- and (S)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-phenyl]-acrylic acid methyl ester (4.866 g, 14 mmol) in ethanol (70 ml). After the mixture was stirred for 6 h and neutralized with K2CO3 solution, the solvent was evaporated and the crude was dissolved in ethylacetate, washed with brine, water, and dried over Na2SO4. Evaporation of the solvent gave (E)-2-[2-(3-hydroxy-propenyl)-phenyl]-3-methoxy-acrylic acid methyl ester (3.4 g, 93%) as a white solid, m.p. 78-80°. IR (YBr): 1683, 1619 cm-1. MS (EI): 216 (M-MeOH).

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe crude was dissolved in ethylacetate
  3. washwashed with brine, water
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-681b0df33f074b55a1f73e4fe22fa68b
Source dataset
uspto-grants-2000_07
Patent number
US06084120

Reaction notes

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