Hydrochloric Acid → HCID 9866384, compound

HRID 2268111Notes

Reaction equation

HRID 2268111 reaction equation
C([O:3][C:4](=[O:32])/[CH:5]=[C:6](\[CH3:31])/[CH:7]=[CH:8]/[CH:9]=[C:10](\[C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]=1[O:26][CH2:27][CH2:28][CH2:29][CH3:30])/[CH3:11])C.[OH-].[Na+].Cl>C(O)C>[C:22]([C:14]1[C:13]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[C:12](/[C:10](/[CH3:11])=[CH:9]\[CH:8]=[CH:7]\[C:6](\[CH3:31])=[CH:5]\[C:4]([OH:32])=[O:3])[CH:17]=[C:16]([C:18]([CH3:20])([CH3:21])[CH3:19])[CH:15]=1)([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9889483HCID 9889483, compound

Product 1

HCID 9866384HCID 9866384, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

520 mg of (2E,4E,6Z)-7-(3,5-di-tert.-butyl-2-butyloxyphenyl)-3,7-dimethyl-2,4,6-heptatrienoic acid ethyl ester was suspended in 5 ml ethanol and treated with 5 ml 6N NaOH and refluxed for 1.5 hr. This was cooled and acidified to pH 3 with dilute HCl . The solid which precipitated was extracted into chloroform. The organic portion was washed with water, dried (Na2SO4), and had the solvent removed. This gave a solid which was crystallized from methylene chloride/hexane to give (2E,4E,6Z)-7-[3,5-di-tert.butyl-2-butyloxyphenyl]-3-methyl-2,4,6-octatrienoic acid. 1H NMR (CDCl3) δ 7.08 (dd, 4H, aromatics), 6.65 (dd, 1H,H-5), 6.22 (d, 1H,H-4), 6.18 (d, 1H,H-6), 3.7 (dt, 2H, —OCH2—), 2.24 (s, 3H), 2.15 (s, 3H). M.p. 148-151° C.

Workup

  1. temperaturerefluxed for 1.5 hr
  2. temperatureThis was cooled
  3. customThe solid which precipitated
  4. extractionwas extracted into chloroform
  5. washThe organic portion was washed with water
  6. dry with materialdried (Na2SO4)
  7. customremoved
  8. customThis gave a solid which
  9. customwas crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-127eb2e8bd9f4362955647b82557a330
Source dataset
uspto-grants-2001_12
Patent number
US06326397B1

Reaction notes

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