Hydrochloric Acid → HCID 13076858, compound

HRID 1278286Notes

Reaction equation

HRID 1278286 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[OH:6][C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].Cl>CCOCC>[Cl:21][C:18]1[CH:19]=[CH:20][C:7]([OH:6])=[C:8]([C:9]([CH2:3][CH:2]=[CH2:1])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[OH:10])[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6799Chlorohydroxy benzophenoneHCID 178455850HCID 178455850, compound

Product 1

HCID 13076858HCID 13076858, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

360 ml of an ether solution titrating 1 M/liter of allyl magnesium bromide were added dropwise with stirring to a mixture of 40 g of 2-hydroxy-5-chloro-benzophenone and 400 ml of anhydrous ether and the suspension was iced and stirred at room temperature for 16 hours. 180 ml of 2 N hydrochloric acid were added to the mixture and the decanted organic phase was washed with water, dried over mangesium sulfate and evaporated to dryness under reduced pressure. The oil residue was chromatographed over silica gel and was eluted with methylene chloride to obtain 18.9 g of 5-chloro-2-hydroxy-α-(2-propenyl)-α-phenyl-benzene-methanol.

Workup

  1. additionwere added dropwise
  2. washthe decanted organic phase was washed with water
  3. dry with materialdried over mangesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe oil residue was chromatographed over silica gel
  6. washwas eluted with methylene chloride

Sources & evidence

ORD record
ord-1cc53fde9a4c46db95cf304fabd3eba9
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

Loading…