Acetic Acid → HCID 23349112, compound

HRID 1855798Notes

Reaction equation

HRID 1855798 reaction equation
C([O:3][C:4](=[O:23])/[CH:5]=[C:6](\[CH3:22])/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:21])/[CH:11]=[CH:12]/[C:13]1[C:17]([CH3:18])=[C:16]([CH3:19])[O:15][C:14]=1[CH3:20])C.[OH-].[K+].C(O)(=O)C>C(O)C.O>[CH3:22]/[C:6](/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:21])/[CH:11]=[CH:12]/[C:13]1[C:17]([CH3:18])=[C:16]([CH3:19])[O:15][C:14]=1[CH3:20])=[CH:5]\[C:4]([OH:23])=[O:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 86737131HCID 86737131, compound

Product 1

HCID 23349112HCID 23349112, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(E,E,E,E)-3,7-Dimethyl-9-(2,4,5-trimethyl-3-furyl)-2,4,6,8-nonatetraenoic acid ethyl ester (2.8 g.) was dissolved in ethanol (50 ml.) treated with potassium hydroxide (1.6 g.) in water (5 ml.) and heated at reflux for 30 minutes. After cooling to room temperature, water followed by acetic acid (until acid) was added and the solids were filtered off. Crystallization from ethylacetate gave pure (E,E,E,E)-3,7-dimethyl-9-(2,4,5-trimethyl-3-furyl)-2,4,6,8-nonatetraenoic acid (1.5 g.) m.p. 213°-214°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. additionwas added
  4. filtrationthe solids were filtered off
  5. customCrystallization from ethylacetate

Sources & evidence

ORD record
ord-417347b556594a599a336cd843e5179f
Source dataset
uspto-grants-1980_08
Patent number
US04216312

Reaction notes

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