Diethyl Ether → 3-(3-Hydroxypropyl)benzonitrile

HRID 2210732Notes

Reaction equation

HRID 2210732 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](O)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].CCOCC.[OH-].[Na+]>O>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 138542693-Cyanobenzenepropanoic acid2×

Product 1

HCID 138542623-(3-Hydroxypropyl)benzonitrileYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into an oven-dried 500 ml flask with 2-neck adapter and stirring bar, 12.9 g of 3-(3-cyanophenyl)propanoic acid (the product of step (a)) was placed. The system was flushed with argon gas; then 84 ml tetrahydrofuran was added. The resulting mixture was stirred until the acid was dissolved. After cooling for about ten minutes with an ice bath, 88 ml borane-tetrahydrofuran was added in two 44 ml portions over a 20 minute period. The reaction mixture was stirred for 20 minutes in an ice bath and then quenched by the addition of about 17 ml water dropwise. The mixture was stripped to give an oil with white crystals. Ether (200 ml) and a solution of 8.8 g (0.22 mole) sodium hydroxide in 150 ml water were added. The organic phase was separated. The aqueous layer was extracted with an additional 35 ml ether. The combined ether extracts were dried over sodium sulfate, filtered, and stripped. The resulting oil was distilled in a Kugelrohr apparatus, the fraction bpt. 95°-110° C. was collected to give 11.5 g of the above-identified product.

Workup

  1. customThe system was flushed with argon gas
  2. additionthen 84 ml tetrahydrofuran was added
  3. stirringThe resulting mixture was stirred until the acid
  4. dissolutionwas dissolved
  5. temperatureAfter cooling for about ten minutes with an ice bath
  6. addition88 ml borane-tetrahydrofuran was added in two 44 ml portions over a 20 minute period
  7. stirringThe reaction mixture was stirred for 20 minutes in an ice bath
  8. customquenched by the addition of about 17 ml water dropwise
  9. customto give an oil with white crystals
  10. customThe organic phase was separated
  11. extractionThe aqueous layer was extracted with an additional 35 ml ether
  12. dry with materialThe combined ether extracts were dried over sodium sulfate
  13. filtrationfiltered
  14. distillationThe resulting oil was distilled in a Kugelrohr apparatus
  15. custom95°-110° C. was collected

Sources & evidence

ORD record
ord-1f943674511f47e6a15633aad6efe0d5
Source dataset
uspto-grants-1995_10
Patent number
US05460605

Reaction notes

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