Oxalic Acid → 16-(m-Methylphenoxy)-hexadeca-5,8,11,14-tetraynoicacid
Reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][C:10]#[C:11][CH2:12][C:13]#[C:14][CH2:15][C:16]#[C:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1.CC1C=CC(OCC#CCC#CCC#CCC#CCCCC(O)=O)=CC=1.O1CCCCC1OC1CCCCO1.C(O)(=O)C(O)=O>C(OCC)(=O)C>[CH3:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[O:19][CH2:18][C:17]#[C:16][CH2:15][C:14]#[C:13][CH2:12][C:11]#[C:10][CH2:9][C:8]#[C:7][CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
185 mg of 16-(m-methylphenoxy)hexadeca-5,8,11,14-tetraynoic acid methyl ester was treated with 21 ml of a pH 6.7 buffer solution (prepared as described in Example 1) and 1.98 g of Sigma Lipase, Type VII, from Candidacylindracea and sonicated for 30 minutes at room temperature. The reaction mixture was then transferred to a separatory funnel with ethyl acetate (200 ml) and acidified to pH ~3 with a saturated solution of oxalic acid. The organic layer was separated, dried over sodium sulfate and the solvent removed in vacuo. The residue was purified by thin layer chromatography in silica gel with a Chromatatron (model 7924, Harrison Research, Palo Alto, CA) using hexane:ethyl acetate:acetic acid (70:30:1) as the eluant, yielding 16-(m-methylphenoxy)-hexadeca-5,8,11,14-tetraynoicacid, as an oil. The product was stored in dry ice.
Workup
- customsonicated for 30 minutes at room temperature
- customThe organic layer was separated
- dry with materialdried over sodium sulfate
- customthe solvent removed in vacuo
- customThe residue was purified by thin layer chromatography in silica gel with a Chromatatron (model 7924, Harrison Research, Palo Alto, CA)
Sources & evidence
- ORD record
- ord-9948b88d822341fca8692f5a3032818d
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04867915
Reaction notes
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