Oxalic Acid → HCID 14578982, compound

HRID 1607807Notes

Reaction equation

HRID 1607807 reaction equation
C[O:2][C:3](=[O:26])[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]=[CH:22][CH:21]=1.O1CCCCC1OC1CCCCO1.C(O)(=O)C(O)=O>C(OCC)(=O)C>[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:26])=[O:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 263182Tetrahydropyranyl etherHCID 14578981HCID 14578981, compound

Product 1

HCID 14578982HCID 14578982, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

540 mg of 16-phenoxyhexadeca-5,8,11,14-tetraynoic acid methyl ester weretreated with 64 ml of a pH 6.7 buffer solution (disodium hydrogen phosphate-potassium dihydrogen phosphate) obtained as described in Example1. The emulsion was vigorously stirred and 6.17 g of Sigma Lipase, Type VII, from Candida cylindracea was added, stirring for 8 hours at room temperature. The reaction mixture was then transferred to a separatory funnel with ethyl acetate (100 ml), and then acidified with saturated solution of oxalic acid. The organic phase was separated, dried over sodium sulfate and the solvent removed under vacuo. The residue was purified by TLC on silica gel with a Chromatotron using hexane:ethyl acetate:acetic acid (60:40:1) as the eluant. The crude product was crystallized from benzene-hexane, to yield 16-phenoxyhexadeca-5,8,11,14-tetraynoic acid. M.P. 74°-76° C. (dec.). The product was stored in dry ice.

Workup

  1. customobtained
  2. stirringstirring for 8 hours at room temperature
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under vacuo
  6. customThe residue was purified by TLC on silica gel with a Chromatotron
  7. customThe crude product was crystallized from benzene-hexane

Sources & evidence

ORD record
ord-ddb81813b2104acf8a1e702dac4736a3
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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