Acetic Acid → 4-Benzylidenecyclohexanone

HRID 1735273Notes

Reaction equation

HRID 1735273 reaction equation
[C:1]1([CH:7]=[C:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>O>[C:1]1([CH:7]=[C:8]2[CH2:17][CH2:16][C:11](=[O:12])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 154177378-Benzylidene-1,4-dioxaspiro[4.5]decane

Product 1

HCID 197051964-Benzylidenecyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an alternate method, when n is the bridging group --CH2 --, the 8-phenylmethylene-1,4-dioxaspiro[4.5]decane is treated with acetic acid and water as previously described, yielding the corresponding 4-phenylmethylenecyclohexanone. The cyclohexanone is then reduced with hydrogen gas in the presence of 10% palladium on charcoal (Degussa type), yielding the corresponding 4-phenylmethylcyclohexanol, which is in turn treated with sodium dichromate and sulfuric acid in water, affording the 4-phenylmethylcyclohexanone. The 4-phenylmethylcyclohexanone is then reacted with cyanoguanidine, as previously described, yielding the targeted 2,4-diamino-6-phenylmethyl-5,6,7,8-tetrahydroquinazoline. Example 3 provides a detailed description of how this reaction is conducted.

Sources & evidence

ORD record
ord-09372f2f1213435a898bc50868aace63
Source dataset
uspto-grants-1996_07
Patent number
US05536725

Reaction notes

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