Diethyl butylmalonate → Phytanic Acid

HRID 637277

Reaction equation

HRID 637277 reaction equation
C(C(C(OCC)=O)C(OCC)=[O:10])C1C=CC=CC=1.C(C(C(OCC)=O)C(OCC)=O)CCC.CC(CCCCCCCC)C(O)=O.C(C(CCCC)(CCCCCCCCCC)C(O)=O)CCC.C(C(CCCCCCCCCC)C(O)=O)CCC.[CH3:87][CH:88]([CH2:90][CH2:91][CH2:92][C@H:93]([CH2:95][CH2:96][CH2:97][C@H:98]([CH2:100][CH2:101][CH2:102]/[C:103](=[CH:105]/[CH2:106][OH:107])/[CH3:104])[CH3:99])[CH3:94])[CH3:89]>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[CH3:104][CH:103]([CH2:102][CH2:101][CH2:100][CH:98]([CH3:99])[CH2:97][CH2:96][CH2:95][CH:93]([CH3:94])[CH2:92][CH2:91][CH2:90][CH:88]([CH3:87])[CH3:89])[CH2:105][C:106]([OH:10])=[O:107]

Participants

9

Reactant 6

HCID 67244Diethyl butylmalonateHCID 69090Diethyl 2-benzylpropanedioateHCID 91167Decanoic acid, 2-methyl-HCID 5280435PhytolHCID 124241272-butyldodecanoic acidHCID 190878952,2-Dibutyldodecanoic acid

Product 1

HCID 26840Phytanic Acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

The 2-benzylalkanoic and 2-butylalkanoic acids were prepared by the malonic ester method starting from diethyl benzylmalonate or diethyl butylmalonate and the appropriate alkyl bromide. The procedure used was analogous to that for the preparation of 2-methyldecanoic acid. Preparation of 2,2-dibutyldodecanoic acid was accomplished by alkylation of 2-butyldodecanoic acid using the method of Pfeffer, Silbert, and Chirinko. Hydrogenation of phytol followed by oxidation of the resulting saturated alcohol with a solution of chromium trioxide in acetic acid gave 3,7,11,15-tetramethylhexadecanoic acid.

Sources & evidence

ORD record
ord-7c1a0b002e334083948a27da8d74ec1b
Source dataset
uspto-grants-1985_12
Patent number
US04556495

Linked notes

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