Ethanol → Dehydroabietic Acid

HRID 1744410Notes

Reaction equation

HRID 1744410 reaction equation
[CH3:1][CH:2]([C:4]1[CH2:13][CH2:12][C@H:11]2[C:6](=[CH:7][CH2:8][C@H:9]3[C@@:17]([C:19]([OH:21])=[O:20])([CH3:18])[CH2:16][CH2:15][CH2:14][C@@:10]32[CH3:22])[CH:5]=1)[CH3:3].CO.C(O)C.C(O)=CC>[Pd].C1C=CC=CC=1.C(O)(=O)C>[CH3:3][CH:2]([C:4]1[CH:13]=[CH:12][C:11]2[C@@:10]3([CH3:22])[CH2:14][CH2:15][CH2:16][C@:17]([C:19]([OH:21])=[O:20])([CH3:18])[C@@H:9]3[CH2:8][CH2:7][C:6]=2[CH:5]=1)[CH3:1]

Participants

8

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 10569Abietic AcidHCID 143500Hydroxypropylene

Product 1

HCID 94391Dehydroabietic Acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

said abietic acid at 200–300° C. for 1–5 hours with the catalyst of 0.1–5% (wt) of 5%–10% palladium/carbon, or incubating directly at 220–380° C. After incubation and cooling down, adding 0.5 to 10-fold (volume) solvent, said solvent can be any one of methanol, ethanol, propenol, acetyester acetic acid, benzene and methbenzene, keeping refluxed for 1–3 hours, filtering when it is warm, cooling down, allowing it to stand for overnight and be crystallized. Dehydroabietic acid is obtained after filtering.

Workup

  1. customat 200–300° C.
  2. customfor 1–5 hours
  3. customincubating directly at 220–380° C
  4. temperatureAfter incubation and cooling down
  5. additionadding 0.5 to 10-fold (volume) solvent
  6. temperaturekeeping refluxed for 1–3 hours
  7. filtrationfiltering when it
  8. temperatureis warm
  9. temperaturecooling down
  10. custombe crystallized

Sources & evidence

ORD record
ord-a674de46ce834a52b48eb19e4e6e755e
Source dataset
uspto-grants-2006_03
Patent number
US07015343B2

Reaction notes

Loading…