HCID 53766659, compound → Caffeic Acid

HRID 1703572Notes

Reaction equation

HRID 1703572 reaction equation
OC1C=C(C=CC=1[C:13](=[O:24])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=1)C=CC(O)=O.[OH:25]C1C=CC(C=CC(O)=O)=CC=1C(=O)C=CC1C=CC(O)=C(O)C=1>>[C:13]([OH:24])(=[O:25])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=1

Participants

3

Reactant 2

HCID 53766659HCID 53766659, compoundHCID 54450021HCID 54450021, compound

Product 1

HCID 689043Caffeic Acid

Procedure

Fraction 2a was chromatographed on #3 Whatman paper, eluting with butanol-acetic acid-water (6:1:4) to separate any remaining caffeic acid. The eluate was concentrated and chromatographed on #3 Whatman paper. Elution with ethyl formate-acetic acid-toluene (4:1:5) produced the two isomers of the dimer in the following amounts: 73 mg. of 3-hydroxy-4-(3',4'-dihydroxycinnamoyl)-cinnamic acid, decomp. 135°-140° C. and 68 mg. of 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid, decomp. 135°-140° C. The structural identity of the compounds was confirmed using ultraviolet scanning and nuclear magnetic resonance (NMR).

Workup

  1. customFraction 2a was chromatographed on #3 Whatman paper
  2. washeluting with butanol-acetic acid-water (6:1:4)
  3. customto separate any remaining caffeic acid
  4. concentrationThe eluate was concentrated
  5. customchromatographed on #3 Whatman paper
  6. washElution with ethyl formate-acetic acid-toluene (4:1:5)
  7. customproduced the two isomers of the dimer in the following amounts
  8. custom135°-140° C. and 68 mg
  9. custom135°-140° C

Sources & evidence

ORD record
ord-157fb092d68844ce9a74fd962a9e5cdd
Source dataset
uspto-grants-1978_11
Patent number
US04124724

Reaction notes

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