Hydrochloric Acid → 4-Methyl-6-hydroxy-2,4-hexadien-1-al

HRID 1729840Notes

Reaction equation

HRID 1729840 reaction equation
C(OC(O)O)C.C([O:9][CH:10](OCC)[C:11]#[C:12][C:13]([CH3:17])=[CH:14][CH2:15][OH:16])C.Cl>[Pd]>[CH3:17][C:13](=[CH:14][CH2:15][OH:16])[CH:12]=[CH:11][CH:10]=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5231668OrthoameisensaureathylesterHCID 544982151,1-Diethoxy-4-methyl-4-hexen-2-yn-6-ol

Product 1

HCID 538961484-Methyl-6-hydroxy-2,4-hexadien-1-al

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Trans 3-methyl-3-penten-1-in-5-ol is reacted with orthoformic acid ethyl ester. The resulting 1,1-diethoxy-4-methyl-4-hexen-2-in-6-ol is partially hydrogenated by means of a deactivated palladium catalyst, followed by treatment with hydrochloric acid to form 4-methyl-6-hydroxy-2,4-hexadien-1-al. Reaction with α-carbethoxy-ethylene-triphenyl-phosphoran yields 2,6-dimethyl-8-hydroxy-2,4,6-octatrien-1-oic acid ethyl ester, which can be oxidized by means of manganous oxide to 2,6-dimethyl-8-oxo-2,4,6-octatrien-1-oic acid ethyl ester.

Sources & evidence

ORD record
ord-fe96b096c1204fa18bab51a874324af9
Source dataset
uspto-grants-1976_11
Patent number
US03989758

Reaction notes

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