Ethanol → HCID 58388140, compound

HRID 931092Notes

Reaction equation

HRID 931092 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]=[O:12].[O-2].[Ca+2].[CH2:15]([OH:17])C>>[CH2:7]([C:8]([CH2:15][OH:17])([CH2:11][OH:12])[CH2:9][OH:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 7707BenzenepropanalHCID 6850728Calciumoxide

Product 1

HCID 58388140HCID 58388140, compound

Procedure

A solution of 3-phenylpropanal (100 g, 0.7 mol), formaldehyde (540 mL, 7.5 mol) and calcium oxide (56 g, 1 mol) in ethanol (1 L) was stirred at 40° C. under nitrogen for 18 h. The reaction mixture was filtered and the filtrate was concentrated. Water (1 L) was added to the residue. The mixture was extracted with ethyl acetate (1 L×3), the combined organic layers were concentrated and purified via silica gel chromatography (petroleum ether/ethyl acetate 3:1) to afford 2-benzyl-2-(hydroxymethyl)propane-1,3-diol as a white solid (90 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionWater (1 L) was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (1 L×3)
  5. concentrationthe combined organic layers were concentrated
  6. custompurified via silica gel chromatography (petroleum ether/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-0599da10fcf7420a862868bc8df264d1
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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