Ethanol → Ethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

HRID 2369726Notes

Reaction equation

HRID 2369726 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5])[OH:2].[CH2:10](O)[CH3:11]>>[CH2:1]([C:3]([CH2:8][OH:9])([CH3:7])[C:4]([O:6][CH2:10][CH3:11])=[O:5])[OH:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 78501Dimethylolpropionic acid

Product 1

HCID 23370761Ethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

Procedure

2,2-Bis(methylol)propionic acid (bis-MPA; MW 134.1, 22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct. After the solution was dried over MgSO4 and evaporated, ethyl 2,2-bis(methylol)propionate (EtMPA) was obtained as a clear and colorless liquid (21.1 g, 86%).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe resins were then filtered out
  3. customthe filtrate was evaporated
  4. additionMethylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct
  5. dry with materialAfter the solution was dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-23b18b99734d40078b3848f95045eef0
Source dataset
uspto-grants-2014_04
Patent number
US08709466B2

Reaction notes

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