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

HRID 454787Notes

Reaction equation

HRID 454787 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 (bisMPA; molecular weight 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-83a00495ca07429d8486240bd40135f5
Source dataset
uspto-grants-2013_07
Patent number
US08496946B2

Reaction notes

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