Hydrochloric Acid → 2-[4-(Benzyloxy)phenyl]propane-1,3-diol

HRID 1619434Notes

Reaction equation

HRID 1619434 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:21](OCC)=[O:22])[C:16](OCC)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH2:21][OH:22])[CH2:16][OH:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2823246Diethyl 2-(4-(benzyloxy)phenyl)malonateHCID 4311764Sodium borohydride

Product 1

HCID 675171722-[4-(Benzyloxy)phenyl]propane-1,3-diolYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of diethyl 2-(4-(benzyloxy)phenyl)malonate (20 gm, 0.0585 mole) in ethanol (200 ml) was added sodium borohydride (17.4 gm, 0.4678 mole) in portions at 0° C. and the reaction mixture was stirred for 4 hrs at 30° C. The reaction mixture was poured into ice cold water, acidified with conc. HCl and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and concentrated under reduced pressure to provide 14.5 gm of product as white solid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d33caf6a0ff42b68d335acfda703674
Source dataset
uspto-grants-2014_07
Patent number
US08772302B2

Reaction notes

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