1-Naphthaldehyde → 2,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol

HRID 1815666Notes

Reaction equation

HRID 1815666 reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-:13].[K+]>C(O)C>[CH3:2][C:1]([CH3:11])([CH2:10][OH:13])[CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[OH:12]

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 225011452,2-Dimethyl-1-(1-naphthyl)-1,3-propanediolYield 196.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Naphthoaldehyde (57.72 g, 0.37 mol) and isobutylaldehyde (55.0 g, 0.76 mol) was mixed and 85% potassium hydroxide (24.5 g, 0.37 mol) dissolved in ethanol (340 ml) was added dropwise thereto with stirring. Exothermic reaction started immediately, and the temperature reached to 65° C. and then decreased. After dropping for about 15 min, the mixture was stirred at 55° C. for 4.5 hr. The reaction solution was concentrated, and water (300 ml) was added thereto. The mixture was extracted with chloroform (200 ml) twice. The extract was washed with saturated brine, dehydrated with anhydrous sodium sulfate and concentrated to give the title compound as a brown oil (83.62 g, yield 98.1%).

Workup

  1. additionwas added dropwise
  2. customExothermic reaction
  3. customreached to 65° C.
  4. stirringthe mixture was stirred at 55° C. for 4.5 hr
  5. concentrationThe reaction solution was concentrated
  6. additionwater (300 ml) was added
  7. extractionThe mixture was extracted with chloroform (200 ml) twice
  8. washThe extract was washed with saturated brine
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-28b591f1464a47eea0835154a417d6cf
Source dataset
uspto-grants-2005_04
Patent number
US06878831B2

Reaction notes

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