Triethylamine → 4-[(e)-2-Methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoate

HRID 1249960Notes

Reaction equation

HRID 1249960 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].S(Cl)(Cl)=O.O[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C=O)C.ClCCl>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=2)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 92203Methyl p-coumarateHCID 5444524-(3-Butenyloxy)benzoic acid

Product 1

HCID 183291964-[(e)-2-Methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoateYield 79.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

8.7 g (0.045 mol) of 4-(but-3-enyloxy)-benzoic acid were treated with 76 ml of thionyl chloride and 2 drops of DMF and boiled under reflux for 3.5 hours. The excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum. The residual acid chloride was taken up in 10 ml of dichloromethane and slowly added dropwise at 0° C. to a mixture of 7.59 g (0,042 mol) of methyl 3-(4-hydroxyphenyl)-acrylate (Example 1) and 6 ml of triethylamine in 40 ml of dichloromethane. The batch was stirred at room temperature overnight. The white precipitate in the reaction mixture was dissolved by the addition of dichloromethane. The organic phase was washed repeatedly with water, dried over Na2SO4 and evaporated to dryness. For purification, the residue was chromatographed on silica gel with dichloromethane and subsequently recrystallized from ethanol. 12.65 g of 4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoate were isolated as a white powder; phase succession (° C.): C 103 N138 I.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customThe excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum
  3. washThe organic phase was washed repeatedly with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customFor purification
  7. customthe residue was chromatographed on silica gel with dichloromethane
  8. customsubsequently recrystallized from ethanol

Sources & evidence

ORD record
ord-91453b1440f14057ac32c15d19e30945
Source dataset
uspto-grants-2002_01
Patent number
US06335409B1

Reaction notes

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