Benzaldehyde → Phosphine

HRID 276162

Reaction equation

HRID 276162 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.N[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C1C=CC=CC=1.C=CCCCC.C1(C)C=CC=CC=1.[PH3:46]>>[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].[PH3:46]

Participants

9

Reactant 7

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 1140TolueneHCID 6115AnilineHCID 115971-HexeneHCID 153472-Amino-3-methylpyridineHCID 24404Phosphine

Product 2

HCID 24404PhosphineHCID 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, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), the mixture in a 500 ml pressure reactor was stirred at normal temperature for 2-3 minutes and then [Rh(C8H14)2Cl]2 0.01 mmol and various phosphine ligands 0.025 mmol as shown in the following table 7 were introduced into each reactor. 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, gas chromatography was conducted to determine the yields of heptanophenone, products from various phosphine ligands. The results are given in Table 7, below.

Workup

  1. additionwere introduced into each reactor
  2. stirringwith stirring
  3. customAfter completion of the reaction, gas chromatography

Sources & evidence

ORD record
ord-e7fd9fc248924b249dac1da98ef8d5c3
Source dataset
uspto-grants-2002_03
Patent number
US06353139B1

Linked notes

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