Benzaldehyde → Heptanophenone

HRID 276160

Reaction equation

HRID 276160 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1C(C)=CC=CN=1.C(O)(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C=CCCCC.C1(C)C=CC=CC=1>>[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:8])[CH2:22][CH2:23][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 1140TolueneHCID 115971-HexeneHCID 153472-Amino-3-methylpyridine

Product 1

HCID 74282Heptanophenone

Conditions

Temperature
130 °C

Procedure

Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, 2-amino-3-picoline 0.1 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), various kinds of amines 0.3 mmol as shown in the following table 5, were added to each 500 ml pressure reactor. The mixture was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, column chromatography was conducted to determine the yields of heptanophenone, products according to various amines. The results are given in Table 5, below.

Workup

  1. additionwere added to each 500 ml pressure reactor
  2. stirringwith stirring
  3. customAfter completion of the reaction, column chromatography

Sources & evidence

ORD record
ord-e5e44ed7f59d431392a6aa614d158671
Source dataset
uspto-grants-2002_03
Patent number
US06353139B1

Linked notes

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