Sodium Chloride → [3-(2-Furyl)phenyl]methanol

HRID 2295857Notes

Reaction equation

HRID 2295857 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[BH4-].[Na+].[Cl-].[Na+]>C(O)C.C(Cl)Cl.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 201640Ketone, 3-furyl phenylHCID 4311764Sodium borohydride

Product 1

HCID 11116545[3-(2-Furyl)phenyl]methanolYield 101.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g (0.017 mol) of 3-(2-furanyl)benzaldehyde and 0.66 g (0.017 mol) of sodium borohydride in 30 mL of ethanol was stirred at ambient temperature for 18 hours. The reaction mixture was concentrated under reduced pressure to give a residual oil. The oil was dissolved in a mixture of methylene chloride and water, and was saturated with solid sodium chloride, then extracted with three portions of 100 mL each of methylene chloride. The combined extracts were dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 3.0 g of 3-(2-furanyl)-phenylmethanol.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residual oil
  3. extractionextracted with three portions of 100 mL each of methylene chloride
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0c0d1281a674fcda742df7f4748f042
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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