Hydrochloric Acid → HCID 12788553, compound

HRID 426687Notes

Reaction equation

HRID 426687 reaction equation
[OH-].[Na+].O.[CH3:4]/[C:5](/[CH:11]=[CH:12]/[C:13](/[F:26])=[C:14](\[CH3:25])/[CH:15]=[CH:16]/[C:17]1[C:21]([CH3:22])=[C:20]([CH3:23])[S:19][C:18]=1[CH3:24])=[CH:6]\[C:7]([O:9]C)=[O:8].Cl>C(O)C>[CH3:4]/[C:5](/[CH:11]=[CH:12]/[C:13](/[F:26])=[C:14](\[CH3:25])/[CH:15]=[CH:16]/[C:17]1[C:21]([CH3:22])=[C:20]([CH3:23])[S:19][C:18]=1[CH3:24])=[CH:6]\[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 12788567HCID 12788567, compound

Product 1

HCID 12788553HCID 12788553, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 0.5 g. (12.5 mmol) of sodium hydroxide in 4 ml. of water was added to a solution of 1.0 g. (3 mmole) of methyl 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenoate in 10 ml. of absolute ethanol. The mixture was stirred at 45° C. for 4 hours. The solution was cooled to room temperature, acidified with 3 N hydrochloric acid and filtered. The crude orange solid was purified by silica gel chromatography, euted with hexane-ethyl acetate (3:5 parts by volume) and crystallized from hexane-ethyl acetate (1:1 parts by volume) to give 600 mg. (62% yield) of 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenoic acid orange crystals, m.p. 217°-223° C.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered
  3. customThe crude orange solid was purified by silica gel chromatography
  4. customcrystallized from hexane-ethyl acetate (1:1 parts by volume)
  5. customto give 600 mg

Sources & evidence

ORD record
ord-9a7a629db07c40e5aebb67c577358913
Source dataset
uspto-grants-1979_10
Patent number
US04171318

Reaction notes

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