Hydrochloric Acid → HCID 13565961, compound

HRID 2290812Notes

Reaction equation

HRID 2290812 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]Br)OCC[O:27]1.[Mg].Cl>O.CCOCC.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12](=[O:13])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:26](=[O:27])[CH3:25])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795263,4-Bis(benzyloxy)benzaldehydeHCID 5462224MagnesiumHCID 217705972-(6-Bromohexyl)-2-methyl-1,3-dioxolane

Product 1

HCID 13565961HCID 13565961, compoundYield 24.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 12.7 g of 3,4-dibenzyloxybenzaldehyde and 150 ml of tetrahydrofuran was added dropwise an ether solution of Grignard reagent prepared from 10.4 g of 2-methyl-2-(6-bromohexyl)-1,3-dioxolane and 1.1 g of magnesium at a temperature below 5° C. After stirring the mixture for 2 hours at room temperature, water was added to the mixture and acidifying the mixture by the addition of diluted hydrochloric acid, the reaction mixture thus obtained was extracted with toluene. The extract was washed with water, dried by anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue were added 300 ml of acetone and 0.1 g of p-toluenesulfonic acid, the mixture was stirred overnight at room temperature and concentrated under reduced pressure. The residue was extracted with toluene and the extract was washed with an aqueous 5% sodium hydrogencarbonate solution, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide an oily product. The product was applied to silica gel (500 ml) column chromatography and eluted with a mixture of toluene and ethyl acetate (19:1) to provide 4.4 g of 1-(3,4-dibenzyloxyphenyl)-1,8-nonanedione. Melting point 64°-66° C.

Workup

  1. customthe reaction mixture thus obtained
  2. extractionwas extracted with toluene
  3. washThe extract was washed with water
  4. dry with materialdried by anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue were added 300 ml of acetone and 0.1 g of p-toluenesulfonic acid
  7. stirringthe mixture was stirred overnight at room temperature
  8. concentrationconcentrated under reduced pressure
  9. extractionThe residue was extracted with toluene
  10. washthe extract was washed with an aqueous 5% sodium hydrogencarbonate solution
  11. washwashed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto provide an oily product
  15. washeluted with a mixture of toluene and ethyl acetate (19:1)

Sources & evidence

ORD record
ord-22ec1e06086449f3a1294ac9b0452cce
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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