Methanol → Poly(oxy-1,2-ethanediyl), α-(3,3-dicarboxypropyl)-ω-methoxy-

HRID 1098093Notes

Reaction equation

HRID 1098093 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:20])[CH:7]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:8]([O:10]CC)=[O:9])C.CO>O>[CH3:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][CH:7]([C:8]([OH:10])=[O:9])[C:6]([OH:20])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58583956667871-49-0

Product 1

HCID 20728366Poly(oxy-1,2-ethanediyl), α-(3,3-dicarboxypropyl)-ω-methoxy-Yield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (2.00 g, 50.00 mmol) in water (15 mL) was added to a stirred solution of diethyl[2-(2-methoxyethoxy)ethyl]malonate (Step 1) (2.35 g, 8.96 mmol). The reaction was kept at ambient temperature for 10 minutes before MeOH was removed in vacuo. The resulting solution was acidified to pH=1 by the addition of HCl (5 M). Diethyl ether was added and the two phases were separated. The aqueous phase was extracted three times with diethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to give the title compound as a colourless oil (1.81 g), 1H NMR (300 MHz, CDCl3) δ 7.16 (br s, 2H), 3.58 (m, 7H), 3.40 (s, 3H), 2.23 (m, 2H).

Workup

  1. customwas removed in vacuo
  2. additionThe resulting solution was acidified to pH=1 by the addition of HCl (5 M)
  3. additionDiethyl ether was added
  4. customthe two phases were separated
  5. extractionThe aqueous phase was extracted three times with diethyl ether
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da9005919e9c4b8eae988016e05e4d40
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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