Diethyl phenylmalonate → 2-Phenyl-1,3-propanediol

HRID 589537

Reaction equation

HRID 589537 reaction equation
P([O-])(O)(O)=O.[Na+].[C:7]1([CH:13]([C:19](OCC)=[O:20])[C:14](OCC)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+]>C(O)C.[OH-].[Na+]>[C:7]1([CH:13]([CH2:14][OH:15])[CH2:19][OH:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 66514Diethyl phenylmalonateHCID 4311764Sodium borohydrideHCID 23672064Monosodium phosphate

Product 1

HCID 2541782-Phenyl-1,3-propanediolYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
6 °C

Procedure

Sodium dihydrogen phosphate (58.3 g) was added to a solution of 50 g of diethyl phenylmalonate in 350 ml of ethanol. The mixture was cooled to 5-7° C. and a solution of 16.7 g of sodium borohydride in 38 ml of 0.2% NaOH was gradually added. The mixture was stirred for additional 2 hours and the Ethanol was distilled out. The reaction was quenched by adding 132 ml of water followed by heating to 50° C.-60° C. for 2 hours. The solution was then basified with 50% NaOH and extracted with ethyl acetate. The organic layer was washed with water and evaporated to dryness. The precipitate was crystallized from toluene. 20 g of 2-phenyl-1,3-propanediol was obtained with a yield of 63%.

Workup

  1. distillationthe Ethanol was distilled out
  2. customThe reaction was quenched
  3. additionby adding 132 ml of water
  4. temperatureby heating to 50° C.-60° C. for 2 hours
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. customevaporated to dryness
  8. customThe precipitate was crystallized from toluene

Sources & evidence

ORD record
ord-b88aeaad75c048ccbe383ea0a0fd611f
Source dataset
uspto-grants-2016_01
Patent number
US09233898B2

Linked notes

Loading…