Hydrochloric Acid → HCID 13076857, compound

HRID 1278288Notes

Reaction equation

HRID 1278288 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:20])=[C:10]([CH:19]=1)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].[Cl-].[NH4+].Cl>O1CCCC1.CCOCC>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:20])=[C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH:1]=[CH2:2])[OH:12])[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6799Chlorohydroxy benzophenoneHCID 25517Ammonium ChlorideHCID 178461836HCID 178461836, compound

Product 1

HCID 13076857HCID 13076857, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

225 ml of a filtered solution of 2.5 M/liter of vinyl magnesium chloride in tetrahydrofuran were added dropwise with stirring at -10° C. to a mixture of 58 g of 5-chloro-2-hydroxy-benzophenone and 900 ml of anhydrous ether and the mixture was stirred at room temperature for 16 hours and was refluxed for 3 hours. The mixture was iced and 600 ml of aqueous 10% ammonium chloride solution and 50 ml of concentrated hydrochloric acid were added thereto dropwise. The decanted organic phase was washed twice with 100 ml of water, was dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The oil residue was chromatographed over silica gel and was eluted with methylene chloride to obtain 34.4 g of 5-chloro-2-hydroxy-α-phenyl-α-ethenyl-benzene-methanol.

Workup

  1. temperaturewas refluxed for 3 hours
  2. washThe decanted organic phase was washed twice with 100 ml of water
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customThe oil residue was chromatographed over silica gel
  7. washwas eluted with methylene chloride

Sources & evidence

ORD record
ord-4a0985182d0644ccb9a455226a2101d4
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

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