Salicylideneaniline → Lithium 2-phenyliminomethyl phenolate

HRID 58931Notes

Reaction equation

HRID 58931 reaction equation
CC(C)[O-].[Li+:5].[CH:6](=[N:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9]>C(#N)C>[C:15]1([N:14]=[CH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[O-:9])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[Li+:5]

Participants

4

Reactant 2

HCID 136621SalicylideneanilineHCID 23673350Lithium propan-2-olate

Product 1

HCID 58099172Lithium 2-phenyliminomethyl phenolateYield 459.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Lithium isopropoxide (300 mL, 20.7 g, 66.03 mmol) was added slowly to a solution of N-salicylideneaniline (61.83 g, 66.03 mmol) in dried acetonitrile (200 mL) under nitrogen atmosphere. A pale yellow precipitate was formed and was left stirring overnight. It was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven for 8 hours at 80° C. Giving 61.6 g of product (97% yield). Sublimation (260° C., 10−6 Torr.) yielded an analytical sample (25.1 g from 29.2 g).

Workup

  1. customA pale yellow precipitate was formed
  2. waitwas left
  3. filtrationIt was filtered off
  4. washwashed thoroughly with acetonitrile
  5. customdried in vacuum oven for 8 hours at 80° C

Sources & evidence

ORD record
ord-2ede4bff73b04dfdac058398fe67aaa0
Source dataset
uspto-grants-2016_09
Patent number
US09437828B2

Reaction notes

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