Formic Acid → HCID 67453139, compound

HRID 1441761Notes

Reaction equation

HRID 1441761 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[CH2:8][C:9]#[N:10].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)=O>C(O)C>[C:14]1(=[C:8]([C:7]2[CH:6]=[C:5]([CH3:4])[CH:13]=[CH:12][CH:11]=2)[C:9]#[N:10])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7967CyclohexanoneHCID 76279m-MethylphenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 67453139HCID 67453139, compoundYield 58%

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 3-methyl benzylcyanide (1310 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/157-165° C. yields 12.2 g of product (58% yield), which is further purified by a fine distillation at 0.05 mbar/183° C. to yield 3.95 g (19%) of product as a colourless oil.

Workup

  1. distillationfollowed by a short path distillation at 0.05 mbar/157-165° C.

Sources & evidence

ORD record
ord-671030adcfa7474389ccb1ecfd088c61
Source dataset
uspto-grants-2010_02
Patent number
US07655701B2

Reaction notes

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