Hydrochloric Acid → 1,1-Diphenylbutane-1,4-diol

HRID 1297020Notes

Reaction equation

HRID 1297020 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1(=[O:14])[O:13][CH2:12][CH2:11][CH2:10]1.[Cl-].[NH4+].Cl>C1COCC1>[C:1]1([C:9]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:14])[CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7302Gamma-ButyrolactoneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 966791,1-Diphenylbutane-1,4-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60 ml (120 mmol) of 2 M solution of phenyl magnesium bromide in THF was added dropwise to 4.33 g (50.3 mmol) of γ-butyrolactone in 60 ml of THF for the duration of 50 minutes. After stirring at room temperature overnight, a saturated aqueous ammonium chloride solution and then 2 N hydrochloric acid were added dropwise to the reaction mixture. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1300b65ce05412092a24a55b6cd2266
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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