Oxalic Acid → HCID 53902041, compound

HRID 1288529Notes

Reaction equation

HRID 1288529 reaction equation
[CH:1]([CH:8]1[CH:13]2[CH:9]1[CH2:10][CH:11]([O:14]C1CCCCO1)[CH2:12]2)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)(=O)C(O)=O>CO>[CH:1]([CH:8]1[CH:13]2[CH:9]1[CH2:10][CH:11]([OH:14])[CH2:12]2)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 54186057HCID 54186057, compound

Product 1

HCID 53902041HCID 53902041, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8.5 g. of 6-(1-heptenyl)-3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane (from Example 12) and 700 mg. of oxalic acid in 350 ml. of methanol is stirred at room temperature (about 25° C.) for 7 days. The solution is then evaporated and the residue extracted with diethyl ether. Evaporation of the ether solution gives a quantitative yield of 6-(1-heptenyl)-bicyclo[3.1.0]hexan-3-ol; γ 3375, 3050, 3025, 1625, 1070, 1020, 960, 850 and 725 cm-1.; γ max 197 mmu (heptane), δ 5.2, 4.8 p.p.m. Thin layer chromatographic analysis shows four spots (silica gel, developed with benzene-ether 5:1).

Workup

  1. customThe solution is then evaporated
  2. extractionthe residue extracted with diethyl ether
  3. customEvaporation of the ether solution

Sources & evidence

ORD record
ord-fd4c694ecbf84345afd3af5af201edd7
Source dataset
uspto-grants-1976_10
Patent number
US03988372

Reaction notes

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