Triethylamine → HCID 19391887, compound

HRID 1756892Notes

Reaction equation

HRID 1756892 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH:5]=[C:6]1[CH:16]=[CH:15][CH:14]=[C:8]2[C:9]([O:11][C:12](=O)[CH:7]12)=[O:10].C(N(CC)CC)C>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][CH2:6][C:7]1[CH:12]=[CH:16][CH:15]=[CH:14][C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86748900HCID 86748900, compound2×

Product 1

HCID 19391887HCID 19391887, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

10 g (0.0397 mol) of 2-methoxybenzylidene phthalic anhydride (compound 1) is placed in a 500 ml autoclave. 230 ml of ethanol, 4.02 g (1 eq.) of triethylamine and 20 g of Raney nickel freshly prepared from 40 g of 50% Raney nickel alloy by a conventional method are added. The reaction mixture is stirred under an H2 pressure of 4 kg/cm2 at room temperature for 2 days. After the catalyst is filtered off and washed with ethanol, the filtrate is evaporated. The resulting crude crystals are recrystallized from ethyl acetate-hexane to give 6.548 g (yield 64%) of colorless acicular crystals having a melting point of 118° to 119° C.

Workup

  1. additionare added
  2. filtrationAfter the catalyst is filtered off
  3. washwashed with ethanol
  4. customthe filtrate is evaporated
  5. customThe resulting crude crystals are recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a5fe470fb8ba454f97f43837d5885f3c
Source dataset
uspto-grants-1995_08
Patent number
US05442122

Reaction notes

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