Benzoic Acid → 2-(4-Cyano-3-fluorophenyl)-5-n-heptyl-1,3-dioxane

HRID 246872

Reaction equation

HRID 246872 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[F:11])#[N:2].F[C:13]1[CH:18]=[C:17]([N+]([O-])=O)[CH:16]=[CH:15][C:14]=1[CH3:22].[C:23](O)(=[O:30])[C:24]1C=CC=C[CH:25]=1.FC1C=C(N)C=CC=1C#N.C=NO.FC1C=C(N)C=CC=1C.FC1C=C(C=CC=1C)C#N.FC1C=C(C=CC=1C)C(OCC)=O.FC1C=C(C=CC=1C#N)C(OCC)=O.FC1C=C(C=CC=1C#N)CO.C(C(CO)CO)CCCCCC>C1(C)C=CC=CC=1.O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[O:30][CH2:23][CH:24]([CH2:13][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:22])[CH2:25][O:8]2)=[CH:5][C:4]=1[F:11])#[N:2]

Participants

14

Reactant 11

HCID 243Benzoic AcidHCID 6350NitroneHCID 99573-Fluoro-4-methylanilineHCID 740252-Fluoro-4-nitrotolueneHCID 2255562-Heptylpropane-1,3-diolHCID 5851403-Fluoro-4-methylbenzonitrileHCID 27834134-Amino-2-fluorobenzonitrileHCID 112173392-Fluoro-4-formylbenzonitrileHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrileHCID 13489923Benzoic acid, 3-fluoro-4-methyl-, ethyl esterHCID 21284546Ethyl 4-cyano-3-fluorobenzoate

Product 1

HCID 212845412-(4-Cyano-3-fluorophenyl)-5-n-heptyl-1,3-dioxane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3.0 g of 4-cyano-3-fluorobenzaldehyde obtainable from 2-fluoro-4-nitrotoluene by oxidation to the corresponding benzoic acid, conversion into the corresponding nitrile, reduction to 2-fluoro-4-aminobenzonitrile and conversion of the corresponding diazonium salt with formaldoxime into the aldehyde in accordance with the method of Beech (J. Chem. Soc. 1297 (1954)); the target product is also obtainable from 2-fluoro-4-aminotoluene by conversion into 3-fluoro-4-methylbenzonitrile by the Sandmeyer method, hydrolysis of the nitrile, bromination of the side chain of the ethyl 3-fluoro-4-methylbenzoate obtainable, conversion into the aldehyde by the Sommelet method, conversion of the resulting oxime into ethyl 3-fluoro-4-cyanobenzoate, reduction to 3-fluoro-4-cyanobenzyl alcohol and subsequent oxidation to the target product) and 3.5 g of 2-n-heptylpropane-1,3-diol is heated together with 1 g of strongly acid cation exchanger in 100 ml of toluene for 8 hours using a water separator. The catalyst is then filtered off and the toluene is removed. After customary working-up, 2-(4-cyano-3-fluorophenyl)-5-n-heptyl-1,3-dioxane is obtained.

Workup

  1. filtrationThe catalyst is then filtered off
  2. customthe toluene is removed

Sources & evidence

ORD record
ord-8419d0abd8b5400683e62105600ca19a
Source dataset
uspto-grants-1987_11
Patent number
US04704227

Linked notes

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