Sodium Hydroxide → HCID 59510866, compound

HRID 1157066Notes

Reaction equation

HRID 1157066 reaction equation
C[O:2][C:3]([C:5]1[C:6]([O:20][CH3:21])=[C:7]2[C:12](=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[CH:11]1[CH2:19][CH:8]2[CH:9]=[CH:10]1)=[O:4].[OH-].[Na+]>CO>[CH3:21][O:20][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[C:14]([O:15][CH3:16])[C:13]([O:17][CH3:18])=[C:12]2[C:7]=1[CH:8]1[CH2:19][CH:11]2[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59510871HCID 59510871, compound

Product 1

HCID 59510866HCID 59510866, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 14 (0.591 g, 2.05 mmol) in methanol (50 mL) was added a 4 N NaOH solution (50 mL), and the resulting reaction mixture was heated at reflux for 5 h. Methanol was removed under reduced pressure and a 3 N HCl solution was added to achieve pH 1. The reaction mixture was extracted three times with ethyl acetate, dried over sodium sulfate, and concentrated under reduced pressure to yield 0.567 g of 15 as a brown oil in nearly quantitative yield. 1H NMR (300 MHz, CDCl3): δ=2.18-2.27 (m, 2H, CH2), 3.86 (s, 3H, O—CH3), 3.89 (s, 3H, O—CH3), 3.92 (s, 3H, O—CH3), 4.19-4.22 (m, 2H, CH—CH(C)—CH2), 6.78-6.86 (m, 2H, HC═CH); 13C NMR (75 MHz, CDCl3): δ=47.6 (CH—CH(C)—CH2), 47.9 (CH—CH(C)—CH2), 61.6 (CH3), 62.1 (CH3), 62.5 (CH3), 68.5 (CH2), 117.9, 137.8, 142.4 (HC═CH), 142.9 (HC═CH), 144.2, 147.2, 147.6, 148.6, 170.6; ESI-MS calcd for C15H16O5 [M−H]−: 275.0920. found 275.0910.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 5 h
  4. customMethanol was removed under reduced pressure
  5. additiona 3 N HCl solution was added
  6. extractionThe reaction mixture was extracted three times with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a17d911fe7c14814b4a2230a0b1bf103
Source dataset
uspto-grants-2010_10
Patent number
US07807140B2

Reaction notes

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