Benzaldehyde → HCID 53750027, compound

HRID 328264Notes

Reaction equation

HRID 328264 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.COC1C=CC=CC=1.Cl[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]C(Cl)=O)=[CH:29][CH:28]=1.COC.Cl.N1C=CC=CC=1.C(=O)C1C=CC=CC=1.N1CCCCC1>CO.C(O)(=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:33][C:30]2[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=2)=[CH:4][CH:3]=1

Participants

10

Reactant 7

HCID 240BenzaldehydeHCID 7519AnisoleHCID 8082PiperidineHCID 8254Dimethyl EtherHCID 906924-Chlorophenylacetyl chlorideHCID 2726363HCID 2726363, compoundHCID 10176127Pyridinium chloride

Product 1

HCID 53750027HCID 53750027, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

8 g (0.0324 mole) of 1-(4-hydroxyphenyl)-2-(4-chlorophenyl)ethanone (prepared by Friedel-Craft reaction between methoxybenzene and 4-chlorophenylacetylchloride, followed by demethylation of the methyl ether with pyridine hydrochloride) was treated with 3.44 g (0.0324 mole) of benzaldehyde and 2.58 g (0.304 mole) of piperidine in 15 ml of methanol at 60° C and worked up as under Example IA gave 9.0 g of crude product. 8.5 g of this material on refluxing with 85 ml of glacial acetic acid for 4 hours and was worked up as under Example IB. Trituration with hot methanol and cooling gave 3 g (44.5%) of crystalline material, m.p. 228°.

Workup

  1. customgave 9.0 g of crude product

Sources & evidence

ORD record
ord-702d54b56d274850b7f9f3d8ed631cf4
Source dataset
uspto-grants-1977_04
Patent number
US04016223

Reaction notes

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