HCID 117664395, compound → HCID 117664725, compound

HRID 2199487Notes

Reaction equation

HRID 2199487 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:4]([O:6]C)=[O:5]>[OH-].[Na+].Cl.C(OCC)(=O)C>[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 1

HCID 117664395HCID 117664395, compound

Product 1

HCID 117664725HCID 117664725, compoundYield 90.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Dissolve compound 8 (3 g, 0.0085 mol) in 30 ml 20% aqueous sodium hydroxide solution, heat to reflux for 2 h, cool the solution to stop the reaction. Add in 10% dilute hydrochloric acid to adjust the pH to less than 2 to cause a formation of a large amount of white precipitation, filter and dry the precipitation to obtain a white solid, dissolve it in petroleum ethe/ethyl acetate and recrystallize to obtain 2.6 g white solid (90%). 1H-NMR (400M, CDCl3) δ (ppm): 1.61 (s, 3H), 1.71 (s, 3H), 3.24 (d, J=6.8 Hz, 2H), 3.91 (s, 3H), 5.12 (t, J=6.8 Hz, 1H), 6.78 (s, 1H), 7.00 (d, J=16 Hz, 1H), 7.27 (t, J=7.2 Hz, 1H), 7.38 (t, J=7.2 Hz, 2H), 7.52 (d, J=7.2 Hz, 2H), 7.84 (d, J=16 Hz, 1H), 12.28 (s, 1H). ESI-MS mz: 361.14318 [M+Na]+ (Calcd. for C21H22O4Na: 361.14158).

Workup

  1. temperatureheat
  2. temperatureto reflux for 2 h
  3. temperaturecool the solution
  4. customthe reaction
  5. customa formation of a large amount of white precipitation
  6. filtrationfilter
  7. customdry
  8. customthe precipitation
  9. customto obtain a white solid
  10. customrecrystallize

Sources & evidence

ORD record
ord-a5a986b2cfaf47d8a3ff959e771751c9
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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