Sulfuric Acid → Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-

HRID 1578630Notes

Reaction equation

HRID 1578630 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=1)[C:12](Cl)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C.S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:26][C:12]([C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 108318693,5-Bis(benzyloxy)benzoyl chloride

Product 1

HCID 120098Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
130 °C

Procedure

70 g of 3,5-dibenzyloxy-benzoyl-chloride in dry benzene were slowly added to a solution of diethyl ethoxy-magnesium-malonate prepared in known manner. The reaction mixture was refluxed overnight, and after cooling 300 ml of benzene and 200 ml of 5-N sulphuric acid were added to hydrolyze the mixture. The benzene phase was washed 3 times with water and dried with magnesium sulphate. The benzene was evaporated and the excess of diethyl malonate distilled off under reduced pressure. To the residue 400 ml of dioxane, 80 ml of water and 40 ml of conc. hydrochloric acid were added. The reaction mixture was heated for 24 hours on an oil bath at 130°C. After evaporation a brown oil remained, which crystallized on standing. Recrystallized from ethanol: M.p. 60°-61°C.

Workup

  1. customprepared in known manner
  2. temperatureThe reaction mixture was refluxed overnight
  3. additionwere added to hydrolyze the mixture
  4. washThe benzene phase was washed 3 times with water
  5. dry with materialdried with magnesium sulphate
  6. customThe benzene was evaporated
  7. distillationthe excess of diethyl malonate distilled off under reduced pressure
  8. additionTo the residue 400 ml of dioxane, 80 ml of water and 40 ml of conc. hydrochloric acid were added
  9. customAfter evaporation a brown oil
  10. customwhich crystallized
  11. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-7bf45396e8674fcfaf3d515d88e07dc2
Source dataset
uspto-grants-1976_02
Patent number
US03937838

Reaction notes

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