Sulfuric Acid → HCID 13366430, compound

HRID 1632470Notes

Reaction equation

HRID 1632470 reaction equation
C([O:3][C:4](=[O:29])/[CH:5]=[C:6](\[CH3:28])/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:27])/[CH:11]=[CH:12]/[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][C:21]([F:24])([F:23])[F:22])=[C:15]([CH3:25])[C:14]=1[CH3:26])C.O1CCOCC1.[OH-].[K+].S(=O)(=O)(O)O>CCCCCC>[CH3:28]/[C:6](/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:27])/[CH:11]=[CH:12]/[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][C:21]([F:22])([F:24])[F:23])=[C:15]([CH3:25])[C:14]=1[CH3:26])=[CH:5]\[C:4]([OH:29])=[O:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 13366427HCID 13366427, compound

Product 1

HCID 13366430HCID 13366430, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 15.3 g (0.0375 mol) of ethyl-(2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoate, 76.5 ml of dioxane and 30 ml of 2N methanolic KOH was heated to reflux for 4 hours. The mixture was then poured into 300 ml of ice-H2O and acidified to pH 2 with 2N sulfuric acid. The yellow precipitate was extracted with 3×200 ml of chloroform, washed with sodium chloride solution and dried (MgSO4). Evaporation of the solvent gave a yellow solid, which was treated with 150 ml of hexane and filtered to give 12 g of crude (2E,4E,6E,8E)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoic acid. Recrystallization from 200 ml of ethyl acetate gave 9.25 g of (2E,4E,6E,8E,)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(trifluoromethoxy)phenyl]-nonatetraenoic acid; mp 190°-193° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. extractionThe yellow precipitate was extracted with 3×200 ml of chloroform
  4. washwashed with sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. customgave a yellow solid, which
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6adc383dd5a2463c9ac2eb118c4f312f
Source dataset
uspto-grants-1984_10
Patent number
US04476056

Reaction notes

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