Hydrochloric Acid → HCID 70528399, compound

HRID 1578102Notes

Reaction equation

HRID 1578102 reaction equation
[CH2:1]([O:3]C=O)C.CC[O-].[Na+].[CH3:10][C:11]([CH3:24])([C:13](=[O:23])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH3:12].Cl>C(O)C>[OH:3][CH:1]=[C:14]([O:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[C:13](=[O:23])[C:11]([CH3:24])([CH3:10])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 20517757HCID 20517757, compound

Product 1

HCID 70528399HCID 70528399, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

163 g (2.2 mol) of formic acid ethyl ester were added dropwise to a solution of 136 g of sodium ethylate in 1,500 ml of ethanol at 0° C. 420 g (2 mol) of 2,2-dimethyl-4-(4-fluorophenoxy)-butan-3-one were then slowly stirred in at 0° C. After a reaction time of 24 hours at 0° C., the mixture was allowed to warm to room temperature and was subsequently stirred at this temperature for a further 96 hours. The reaction mixture was poured onto 5,000 ml of ice-water and the organic phase was separated off by extracting with chloroform. Unreacted starting material could be isolated from this chloroform solution and re-used. The aqueous phase was acidified with 10% strength hydrochloric acid, while cooling, and the oil which separated out was taken up in chloroform. The chloroform phase was dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The oil which remained was distilled in vacuo. 170 g (83% of theory, relative to unreacted product) of 1-hydroxy-2-(4-fluorophenoxy)-4,4-dimethyl-penten-3-one of boiling point 101°-102° C./0.6 mm Hg (nD20 =1.5132) were obtained.

Workup

  1. customAfter a reaction time of 24 hours
  2. customat 0° C.
  3. customthe organic phase was separated off
  4. extractionby extracting with chloroform
  5. customcould be isolated from this chloroform solution
  6. temperaturewhile cooling
  7. customthe oil which separated out
  8. dry with materialThe chloroform phase was dried over sodium sulphate
  9. concentrationconcentrated
  10. distillationby distilling off the solvent in vacuo
  11. distillationThe oil which remained was distilled in vacuo

Sources & evidence

ORD record
ord-3d17e04530614963b7b931b415ed3250
Source dataset
uspto-grants-1981_09
Patent number
US04291044

Reaction notes

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