Hydrochloric Acid → HCID 57069668, compound

HRID 1265257Notes

Reaction equation

HRID 1265257 reaction equation
[CH:1]([C:4]1[C:5]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:6]([C:13]([CH3:23])=[CH:14][CH:15]=[CH:16][C:17]([CH3:22])=[CH:18][C:19]([O-:21])=[O:20])[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[CH:1]([C:4]1[C:5]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:6]([C:13]([CH3:23])=[CH:14][CH:15]=[CH:16][C:17]([CH3:22])=[CH:18][C:19]([OH:21])=[O:20])[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86590930HCID 86590930, compound

Product 1

HCID 57069668HCID 57069668, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the crude ethyl-(2E, 4E, 6E)-7-(3,5-diisopropyl-2-n-heptyloxyphenyl)-3-methylocta-2,4,6-trienoate (500 mg, 1.10 mmol) in methanol (5 mL) was hydrolyzed with NaOH (1 mL of 5N aqueous solution) at reflux temperature. After 10 min, the mixture was cooled to room temperature and acidified with a 20% aqueous HCl solution. The solution was concentrated and the aqueous residue was extracted with EtOAc (2×10 mL). The EtOAc layer was washed with water (2×5 mL) and brine (5 mL), dried (MgSO4), filtered and concentrated. The major product (highest running spot by TLC) was isolated by preparative TLC (20% EtOAC-80% hexanes) to give (2E, 4E, 6E)-7-(3,5-diisopropyl-2-n-heptyloxyphenyl)-3-methylocta-2,4,6-trienoic acid (146) 220 mg (47%): TLC (10% MeOH-90% CHCl3) Rf=0.6; 1H NMR (CDCl3) δ 7.04(m, 1H, olefinic), 7.01(s, 1H, ArH ), 6.84(s, 1H, ArH ), 6.35(d, J=11.0 Hz, 1H, olefinic), 6.30(d, J=15.0 Hz, 1H, olefinic), 5.79(s, 1H, olefinic), 3.65(t, J=7.4 Hz, 2H, OCH2), 3.32(m, 1H, CH), 2.84(m, 1H, CH), 2.37(s, 3H, CH3), 2.19(s, 3H, CH3), 1.66(m, 2H, CH2), 1.31(m, 8H, 4CH2), 1.27(d, J=14.0 Hz, 6H, 2CH3), 1.24(d, J=14.0 Hz, 6H, 2CH3), 0.89(t, J=7.5 Hz, 3H, CH3).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe solution was concentrated
  3. extractionthe aqueous residue was extracted with EtOAc (2×10 mL)
  4. washThe EtOAc layer was washed with water (2×5 mL) and brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe major product (highest running spot by TLC) was isolated by preparative TLC (20% EtOAC-80% hexanes)

Sources & evidence

ORD record
ord-d445660e6b894e0f90a7cb3c094d51de
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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