Methanol → HCID 14668942, compound

HRID 899653Notes

Reaction equation

HRID 899653 reaction equation
O1CCC(C[C:8]2[CH:18]=[CH:17][CH:16]=[C:10]3[C:11]([NH:13][C:14](=[O:15])[C:9]=23)=[O:12])OC1.[C:19]([O-:22])(O)=O.[Na+].C([O:27][CH2:28][CH3:29])(=O)C.[CH3:30]O>Cl>[OH:27][CH:28]([CH2:29][CH2:19][OH:22])[CH2:30][N:13]1[C:14](=[O:15])[C:9]2=[CH:8][CH:18]=[CH:17][CH:16]=[C:10]2[C:11]1=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 69158355HCID 69158355, compound

Product 1

HCID 14668942HCID 14668942, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

1,3-dioxane-4-ylmethylphthalimide (95 g, 390 mmol) was dissolved in a saturated solution of hydrochloric acid in methanol (600 mL) and stirred for 2 days at 80° C. The reaction was then cooled to room temperature, and the acid neutralised to pH 7 with solid NaHCO3. Ethyl acetate (1 L) was added and the mixture was filtered to remove salts. The filtrate was then concentrated under reduced pressure and dried overnight in vacuo. The crude was purified through a silica gel plug (1 kg silica) using 2:98 CH3OH:CH2Cl2 eluent to give the desired N-(2,4-dihydroxybutyl)phthalimide as a white solid (45 g, 50%). 1H NMR (MeOD) δ 1.62 (m, 1H), 1.75 (m, 1H), 3.31 (s, 1H), 3.64 (m, 2H), 3.69 (d, 2H, J=5.1 Hz), 4.06 (sept, 1H), 7.79 (m, 2H), 7.85 (m, 2H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationthe mixture was filtered
  3. customto remove salts
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. customdried overnight in vacuo
  6. customThe crude was purified through a silica gel plug (1 kg silica)

Sources & evidence

ORD record
ord-f54566bd7faa4c03be38858354276162
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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