Lithium Hydroxide → 2-Cyanoethoxyethylmethylaniline

HRID 1702428

Reaction equation

HRID 1702428 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Li+].[C:14](#[N:17])[CH:15]=[CH2:16]>C(O)(=O)C>[C:14]([CH2:15][CH2:16][O:1][CH2:2][CH2:3][N:4]([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)#[N:17]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 7855Acrylonitrile2×HCID 623402-(N-Methylanilino)ethanol

Product 1

HCID 542300772-Cyanoethoxyethylmethylaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

In a one-gallon autoclave was charged 1019 gm (6.75 moles) of hydroxyethylmethylaniline, 3 gm of anhydrous lithium hydroxide, and 532 gm (10 moles) of acrylonitrile. The autoclave was sealed and slowly heated to 50° C. until the initial exotherm was over. The reaction was then heated to 65°-70° C. for 6 hours. The reaction contents were cooled to room temperature and made slightly acidic with acetic acid. The reaction contents were then filtered. The crude filtered reaction product was stripped of all excess acrylonitrile under vacuum (15-30 mm Hg) at a temperature not exceeding 80° C. to give the orange liquid, 2-cyanoethoxyethylmethylaniline. Liquid chromatography showed the product to be about 97.4% purity. The IR, NMR, and GC mass spectra of the product were consistent with 2-cyanoethoxyethylmethylaniline.

Workup

  1. customThe autoclave was sealed
  2. temperatureThe reaction was then heated to 65°-70° C. for 6 hours
  3. customThe reaction contents
  4. temperaturewere cooled to room temperature
  5. customThe reaction contents
  6. filtrationwere then filtered
  7. filtrationThe crude filtered
  8. customreaction product
  9. customexceeding 80° C.

Sources & evidence

ORD record
ord-4e6004a95ea4413c926852d1deb39623
Source dataset
uspto-grants-1983_04
Patent number
US04381265

Linked notes

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