Hydrochloric Acid → HCID 21311895, compound

HRID 971844Notes

Reaction equation

HRID 971844 reaction equation
Cl.C1(P(=CC(C=NN)=[O:23])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.N([O-])=[O:28].[Na+].[O:31]1C[CH2:34][CH2:33][CH2:32]1>O>[OH2:23].[CH:15]1([CH2:34][C:33]([CH:32]=[O:31])=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 23668193Sodium NitriteHCID 86736585HCID 86736585, compound

Product 1

HCID 21311895HCID 21311895, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

77 ml of 2N hydrochloric acid are added slowly, with stirring and cooling to 10°-13° (ice-water bath), to a mixture of 15 g of 1-cyclohexyl-3-(triphenylphosphoranylidene-hydrazono-acetone and 7.37 g of sodium nitrite in 120 ml of tetrahydrofuran and 42 ml of water. After another 30 minutes at room temperature the organic solution is separated and the aqueous phase is extracted with methylene chloride. The combined organic solutions are dried over sodium sulphate and evaporated under reduced pressure. The syrupy residue is treated with ether, the resulting triphenyl phosphinoxide is filtered off and the filtrate is evaporated. The residue is chromatographed on a column of 120 g of acid-washed silica gel, elution being carried out with about 3000 ml of a 97:3-mixture of hexane and ethyl acetate to yield the cyclohexylmethyl-glyoxal hydrate as a syrupy product; infra-red absorption spectrum (in methylene chloride): characteristic bands at 2.90-4.1μ (broad); 3.47μ, 3.53μ and 5.80μ; the product is further processed without purification.

Workup

  1. customAfter another 30 minutes at room temperature the organic solution is separated
  2. extractionthe aqueous phase is extracted with methylene chloride
  3. dry with materialThe combined organic solutions are dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. additionThe syrupy residue is treated with ether
  6. filtrationthe resulting triphenyl phosphinoxide is filtered off
  7. customthe filtrate is evaporated
  8. customThe residue is chromatographed on a column of 120 g of acid-washed silica gel, elution

Sources & evidence

ORD record
ord-32b6e21fce864307a6f19d3816df519b
Source dataset
uspto-grants-1979_07
Patent number
US04161476

Reaction notes

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