Tetrahydrofuran → 4,8-Dimethyldeca-4,7,9-trienal

HRID 1658429Notes

Reaction equation

HRID 1658429 reaction equation
O1CCC[CH2:2]1.Cl(O)(=O)(=O)=O.C[CH:12]([CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[C:20]([CH:22]=[CH2:23])[CH3:21])[CH:13]=[O:14]>O>[CH3:2][C:16](=[CH:17][CH2:18][CH:19]=[C:20]([CH:22]=[CH2:23])[CH3:21])[CH2:15][CH2:12][CH:13]=[O:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 53917698HCID 53917698, compound

Product 1

HCID 542205094,8-Dimethyldeca-4,7,9-trienal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 13.4 g. (53 mM) of the C12 -aldehyde diethylacetal, prepared according to the method described in paragraph c), 250 ml. of tetrahydrofuran, 60 ml. of water and and 0.5 ml. of 72% perchloric acid was left for 20 hours at room temperature under nitrogen. Water was added and the mixture was extracted with pentane (3x). The organic layers were washed with 5% NaHCO3 and water, dried over sodium sulphate and evaporated. The remaining oil was distilled to yield 9.2 g. (99%) of 4 methyl-8-vinyl-4,7-nonadienal, b.p. 73°-75°/0.3 Torr. IR(CHCl3): 2720, 1720, 1640, 1605, 995, 905 cm-1. NMR(CCl4): 1.4 - 1.8 ppm (m, 6 H), 2.2 - 2.5 ppm (m, 4H), 2.78 ppm (t, J = 7 cps, 2 H), 4.6 - 5.5 ppm (m, 4 H), 6.20 ppm (about 75%) / 6.64 ppm (about 25%) (2 d of d, J = 10 and 17 cps, 1 H), 9.55 ppm (t, J = about 1.5 cps, 1 H).

Workup

  1. extractionthe mixture was extracted with pentane (3x)
  2. washThe organic layers were washed with 5% NaHCO3 and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. distillationThe remaining oil was distilled
  6. customto yield 9.2 g
  7. customNMR(CCl4): 1.4 - 1.8 ppm (m, 6 H), 2.2 - 2.5 ppm (m, 4H), 2.78 ppm (t, J = 7 cps, 2 H), 4.6 - 5.5 ppm (m, 4 H), 6.20 ppm (about 75%) / 6.64 ppm (about 25%) (2 d of d, J = 10 and 17 cps, 1 H), 9.55 ppm (t, J = about 1.5 cps, 1 H)

Sources & evidence

ORD record
ord-c6fa642763a547c1bd75514753de7d28
Source dataset
uspto-grants-1976_06
Patent number
US03963783

Reaction notes

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