Formic Acid → HCID 67453993, compound

HRID 1441762Notes

Reaction equation

HRID 1441762 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8][C:9]#[N:10].[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O)=O>C(O)C>[C:15]1(=[C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH3:4])[C:9]#[N:10])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7967CyclohexanoneHCID 81496(2-Methoxyphenyl)acetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 67453993HCID 67453993, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Sodium methylate (5.40 g, 0.10 mol) is dissolved in ethanol (70 ml) and 2-methoxy benzylcyanide (14.70 g, 0.10 mol) is added over 2 min. Cyclohexanone (9.80 g, 0.10 mol) is added to the white suspension. The resulting mixture is heated to 85° C. (bath) for 4.5 h. Under icecooling, formic acid (5.0 ml) is added dropwise, upon which the mixture turns colourless. Standard aqueous workup as described in example 1, followed by a short path distillation at 0.05 mbar/137-146° C. yields 8.28 g of product (37% yield) as a viscous oil, from which a crystalline byproduct is separated via crystallization from hexane. The mother liquor is concentrated and the residue subjected to a fine distillation at 0.05 mbar/136° C. to yield the product as colourless oil (1.81 g, 8%).

Workup

  1. distillationfollowed by a short path distillation at 0.05 mbar/137-146° C.

Sources & evidence

ORD record
ord-b3733b062c554c44b7b78de9bfb49e48
Source dataset
uspto-grants-2010_02
Patent number
US07655701B2

Reaction notes

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