Phosphoric Acid → HCID 131710520, compound

HRID 1729845Notes

Reaction equation

HRID 1729845 reaction equation
[CH3:1][C:2](=[CH:5][C:6]#[C:7][C:8]([CH3:15])=[CH:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH:3]=[O:4].[CH2:16]([O:18]C(O)O)[CH3:17].P(=O)(O)(O)O.[C:27]1(C)C=CC(S(O)(=O)=O)=C[CH:28]=1>CCOCC.N1C=CC=CC=1.CO>[CH2:27]([O:4][CH:3]([O:18][CH2:16][CH3:17])[C:2]([CH3:1])=[CH:5][C:6]#[C:7][C:8]([CH3:15])=[CH:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH3:28]

Participants

8

Reactant 4

HCID 1004Phosphoric AcidHCID 6101p-Toluenesulfonic acidHCID 5231668OrthoameisensaureathylesterHCID 131710521HCID 131710521, compound

Product 1

HCID 131710520HCID 131710520, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

36 g. of 2,6-dimethyl-8-acetoxy-2,6-octadien-4-in-1-al is reacted with 31 g. of orthoformic acid ethyl ester and a solution of 0.3 ml. of phosphoric acid and 150 mg. of p-toluenesulfonic acid in 20 ml. of absolute methanol. After standing for 20 hours at room temperature in a nitrogen atmosphere, 2 ml. of absolute pyridine is added and the reaction mixture taken up in ether. The ether extract is washed with sodium bicarbonate solution and water, dried over potassium carbonate, filtered and evaporated under reduced pressure (water pump vacuum). 48 g. of 1,1-diethoxy-2,6-dimethyl-8-acetoxy-2,6-octadien-4-in is obtained (Abs. Max. 269 mμ; E11 = 730).

Workup

  1. extractionThe ether extract
  2. washis washed with sodium bicarbonate solution and water
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. customevaporated under reduced pressure (water pump vacuum)

Sources & evidence

ORD record
ord-2554abe2da804925b507fbf4aec85496
Source dataset
uspto-grants-1976_11
Patent number
US03989758

Reaction notes

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