Hydrochloric Acid → HCID 21311874, compound

HRID 971842Notes

Reaction equation

HRID 971842 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([CH:12]=NN=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:11])=[CH:5][CH:4]=1.N([O-])=[O:35].[Na+].Cl>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([CH:12]=[O:35])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 53820340HCID 53820340, compound

Product 1

HCID 21311874HCID 21311874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.82 g of 1-(4-methoxyphenyl)-3-(triphenylphosphoranylidene-hydrazono)-acetone in 12 ml of tetrahydrofuran is mixed with 0.84 g of pulverized sodium nitrite and the mixture is diluted with 5 ml of water. The resulting suspension is cooled to 0°-5°, treated dropwise over the course of 7 minutes with 8.8 ml of 2N hydrochloric acid and then kept for a further 30 minutes at 0°-5°. The aqueous phase is twice washed with methylene chloride; the combined organic solutions are washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. The oily residue is chromatographed on 40 g of acid-washed silica gel. A small quantity of a by-product is eluted with benzene and, using 1200 ml of a 95:5-mixture of benzene and ethyl acetate, the 4-methoxybenzylglyoxal is obtained in the form of the hydrate, which is an oily product; infra-red absorption spectrum (in methylene chloride): characteristic bands at 2.96μ, 5.79-5.84μ, 6.23μ and 6.63μ. The anhydrous product melts at 139°-140° after recrystallisation from a mixture of chloroform and hexane; ultra-violet absorption spectrum:λ max 333 mμ (in ethanol or hydrochloric acid/ethanol) and λmax 367 mμ (in potassium hydroxide/ethanol); infra-red absorption spectrum (in methylene chloride): characteristic bands at 3.00μ, 5.97μ, 6.09μ, 6.24μ, 6.61μ and 7.15μ.

Workup

  1. temperatureThe resulting suspension is cooled to 0°-5°
  2. washThe aqueous phase is twice washed with methylene chloride
  3. washthe combined organic solutions are washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe oily residue is chromatographed on 40 g of acid-washed silica gel
  7. washA small quantity of a by-product is eluted with benzene

Sources & evidence

ORD record
ord-dc35072be02a4a4dad8bc614436cc84c
Source dataset
uspto-grants-1979_07
Patent number
US04161476

Reaction notes

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