N-methyl-2-pyrrolidone → 4-(3-Hydroxypropyl)benzonitrile

HRID 981138Notes

Reaction equation

HRID 981138 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:12][N:13]1CCCC1=O>Cl>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 105606143-(4-Bromophenyl)propan-1-ol

Product 1

HCID 110841784-(3-Hydroxypropyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-bromobenzenepropanol (9.0 g), cuprous cyanide (4.5 g), cuprous iodide (20 mg), and N-methyl-2-pyrrolidone (20 ml) was heated at 180°-190° for 4 h and poured into a solution of ferric chloride hexahydrate (4.5 g) in hydrochloric acid (2 M; 30 ml). The mixture was heated at 70°-80° for 15 min and extracted with EA (3×100 ml). The extract was washed with hydrochloric acid (2 M; 50 ml), water (50 ml), and aqueous sodium hydroxide (2 M; 50 ml), dried and evaporated. The residue was purified by [C] eluting with cyclohexane-ER (1:1) to give the title compound (3.5 g). T.l.c. (cyclohexane-ER 1:1) Rf 0.15

Workup

  1. temperaturewas heated at 180°-190° for 4 h
  2. temperatureThe mixture was heated at 70°-80° for 15 min
  3. extractionextracted with EA (3×100 ml)
  4. washThe extract was washed with hydrochloric acid (2 M; 50 ml), water (50 ml), and aqueous sodium hydroxide (2 M; 50 ml)
  5. customdried
  6. customevaporated
  7. customThe residue was purified by [C]
  8. washeluting with cyclohexane-ER (1:1)

Sources & evidence

ORD record
ord-6cd2af5d6b664b138c82392a1d208a73
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Reaction notes

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