Hydrochloric Acid → 1,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-

HRID 1636802Notes

Reaction equation

HRID 1636802 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([CH3:20])([C:18]#[N:19])[CH3:17])[CH:15]=1)[C:9](OC)=[O:10])([CH3:5])[CH3:4])#[N:2].[BH4-].[Li+].Cl>O1CCCC1>[OH:10][CH2:9][C:8]1[CH:7]=[C:6]([C:3]([CH3:5])([CH3:4])[C:1]#[N:2])[CH:15]=[C:14]([C:16]([CH3:20])([CH3:17])[C:18]#[N:19])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 19349383Methyl 3,5-bis(1-cyano-1-methyl ethyl)benzoate

Product 1

HCID 193493981,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3,5-bis(1-cyano-1-methyl ethyl)benzoate (5.6 g), lithium borohydride (0.44 g) and tetrahydrofuran (30 ml) was heated under reflux for 2 h. The mixture was cooled and stirred while 2N aqueous hydrochloric acid was added dropwise until the solution remained acidic, and then the mixture was extracted twice with ethyl acetate. The combined extracts were washed with 1N aqueous potasium bicarbonate solution and then dried and evaporated to dryness under reduced pressure to give 2,2'-(5-hydroxymethyl-1,3-phenylene)di(2-methylpropiononitrile), mp. 151°-153°, which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe mixture was cooled
  4. additionwas added dropwise until the solution
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe combined extracts were washed with 1N aqueous potasium bicarbonate solution
  7. customdried
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-500ebb63f9c44b1b9075f9ca11c24cf4
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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