Abietic Acid → Dehydroabietic Acid

HRID 1744411Notes

Reaction equation

HRID 1744411 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]>[Pd].C(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

4

Reactant 1

HCID 10569Abietic Acid

Product 1

HCID 94391Dehydroabietic AcidYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
250 °C

Procedure

115 g of abietic acid was put into a 1000 ml three-neck bottle , and then 2.3 g of 5% palladium/carbon catalyst was added in. The mixture was stirred at 250° C. (oil bath) for 2 hours, after slightly cooled down, 200 ml of 95% ethanol was added. The mixture was refluxed until completely dissolved, filtered when it was warm, allowed to stand still and to be crystallized to give 70 g of dehydroabietic acid after filtered and dried.

Workup

  1. temperatureafter slightly cooled down
  2. temperatureThe mixture was refluxed
  3. dissolutionuntil completely dissolved
  4. filtrationfiltered when it
  5. temperaturewas warm
  6. customto be crystallized

Sources & evidence

ORD record
ord-f7fcbda1bfd24914a21fa340a3271e7e
Source dataset
uspto-grants-2006_03
Patent number
US07015343B2

Reaction notes

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