Hydrochloric Acid → 2-(Phenylmethylene)pentanedial

HRID 1995746Notes

Reaction equation

HRID 1995746 reaction equation
C[O:2][CH:3]1[CH:8]([CH:9](OC)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH:5](OC)[O:4]1.O1CCOCC1.Cl.C(=O)(O)[O-].[Na+]>O>[CH:9](=[C:8]([CH2:7][CH2:6][CH:5]=[O:4])[CH:3]=[O:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 12822119HCID 12822119, compound

Product 1

HCID 30190042-(Phenylmethylene)pentanedial

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 g. 2,6-dimethoxy-3-(α-methoxybenzyl)tetrahydropyran, 300 g. dioxane, 200 ml. water and 40 g. concentrated hydrochloric acid was stirred for 2 hours at 60°-70° C. The solution, which eventually became homogeneous and brown colored, was cooled, neutralized with sodium bicarbonate and the organic layer was separated. The aqueous layer was extracted twice with ether and the combined organic phase was washed until neutral. The solvent was removed and the residue was distilled in vacuo to give 51 g. of the title compound; b.p. 132° C. (1 mm). Yield: 51 g. (73%) (distillation was accompanied by partial decomposition).

Workup

  1. additionA mixture of 100 g
  2. temperatureThe solution, which eventually became homogeneous and brown colored, was cooled
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted twice with ether
  5. washthe combined organic phase was washed until neutral
  6. customThe solvent was removed
  7. distillationthe residue was distilled in vacuo
  8. customto give 51 g

Sources & evidence

ORD record
ord-45a5011d6ff6423997f8269ddda91705
Source dataset
uspto-grants-1983_09
Patent number
US04405795

Reaction notes

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