Hydrochloric Acid → HCID 54466372, compound

HRID 1731184Notes

Reaction equation

HRID 1731184 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:24])[CH:16](O)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.Cl>N1C=CC=CC=1>[C:1]([C:9]1[CH:10]=[C:11]([C:15]([CH3:24])=[CH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 21495604HCID 21495604, compound

Product 1

HCID 54466372HCID 54466372, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6.2 g of ethyl 4-(m-benzoyl-phenyl)-4-methyl-3-hydroxy-butyrate (by process of Step E of Example XIX) in 60 ml of pyridine was heated at 100° C for 3 hours in the presence of 5 ml of phosphorus oxychloride and was then poured into a mixture of 200 g of ice and 65 ml of concentrated hydrochloric acid. The mixture was extracted with ether and the ether phase was washed with water, then with an aqueous saturated sodium bicarbonate solution and then water until the wash water was neutral. The solution was dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure to obtain 5.35 g of ethyl 4-(m-benzoyl-phenyl)-4-methyl-3-butenoate.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe ether phase was washed with water
  3. dry with materialThe solution was dried over sodium sulfate
  4. additiontreated with activated carbon
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5e5600c077d84b6598c848f20e7d6ed5
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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