Benzene → HCID 10943869, compound

HRID 328348Notes

Reaction equation

HRID 328348 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.[NH:14]1CC[CH2:16][CH2:15]1.C1C=CC=CC=1.ClCC#N>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH:10]2[CH2:16][C:15]#[N:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 7856ChloroacetonitrileHCID 31268PyrrolidineHCID 777857-Methoxy-2-tetralone

Product 1

HCID 10943869HCID 10943869, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 7-methoxy-2-tetralone (472 g., 2.68 mole), pyrrolidine (241 g., 3.40 mole) and benzene (2.5l) was refluxed under nitrogen with water separation (Dean-Stark trap) for 2 hrs. and then distilled for a further 1 hr. (1.2l) of distillate). Chloroacetonitrile (324 g., 4.30 mole) was added during 15 mins. and the mixture was refluxed for 4 hrs. and then left at room temperature overnight. Water (1.5l) was added and the mixture was refluxed for 3 hrs. The organic layer was separated while still hot, washed with 3N sulphuric acid (500 ml.) and filtered with suction through a pad of magnesium sulphate. The product crystallized from benzene and from benzene-ether (two crops) as yellow prisms (484 g., 84%); m.p. 97°-99° C.

Workup

  1. distillationand then distilled for a further 1 hr
  2. temperatureand the mixture was refluxed for 4 hrs
  3. temperaturethe mixture was refluxed for 3 hrs
  4. customThe organic layer was separated while still hot,
  5. washwashed with 3N sulphuric acid (500 ml.)
  6. filtrationfiltered with suction through a pad of magnesium sulphate
  7. customThe product crystallized from benzene and from benzene-ether (two crops) as yellow prisms (484 g., 84%)

Sources & evidence

ORD record
ord-8cbca300eedc48d2b2fe91a559b167d6
Source dataset
uspto-grants-1977_04
Patent number
US04017497

Reaction notes

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