Water → N-(10,11-Dihydroxyundecyl)phthalimide

HRID 361476

Reaction equation

HRID 361476 reaction equation
[CH2:1]([N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C[N+]1([O-])CC[O:27]CC1.[OH2:31].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O>[OH:31][CH:10]([CH2:11][OH:27])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 220445222-(Undec-10-en-1-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 12988906N-(10,11-Dihydroxyundecyl)phthalimideYield 71%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of N-(10-Undecenyl)phthalimide (4.97 g, 16.6 mmol), prepared as discribed above, 4-methylmorpholine-N-oxide (8.62 mL, 60% by wt in water, 50.0 mmol) and potassium osmate dihydrate (58 mg, 0.16 mmol) in 100 mL acetone/water (1:1 by wt) was stirred for 16 hours. Water (100 mL) and sodium sulfite (10 g) were added and the resulting solution stirred for an additional hour. The resulting reaction mixture was extracted with dichloromethane (3×80 mL) and the organic phase dried using magnesium sulfate and evaporated to obtain 3.93 g (71% yield) of N-(10,11-Dihydroxyundecyl)phthalimide (inventive compound no. 1108).

Workup

  1. stirringthe resulting solution stirred for an additional hour
  2. customThe resulting reaction mixture
  3. extractionwas extracted with dichloromethane (3×80 mL)
  4. customthe organic phase dried
  5. customevaporated

Sources & evidence

ORD record
ord-f72a386d50494ecc856b4636ca1533b3
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Linked notes

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