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

HRID 2384311Notes

Reaction equation

HRID 2384311 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) (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 filter the unreacted reagent and by-products. The solution was dried over MgSO4, filtered, and the solvent was removed in vacuo. Ethyl 2,2-bis(methylol)propionate was obtained as a clear and colorless liquid (21.1 g, 86% yield).

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
  5. filtrationto filter the unreacted reagent and by-products
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6824d5f793244e198cfde3d7dfbae883
Source dataset
uspto-grants-2012_09
Patent number
US08263715B2

Reaction notes

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