Hydrochloric Acid → HCID 13076850, compound

HRID 1278292Notes

Reaction equation

HRID 1278292 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][C:11]=1[C:22](=[O:24])[CH3:23].Cl.[CH3:26]COCC>>[CH:16]1([C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[C:11]([C:22]([CH3:26])([C:23]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[OH:24])[CH:12]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 130768421-(5-Cyclohexyl-2-hydroxyphenyl)ethan-1-oneHCID 178418255HCID 178418255, compound

Product 1

HCID 13076850HCID 13076850, compound

Procedure

310 ml of an ether solution titrating 0.76 M/liter of phenyl magnesium bromide were added over 1 hour to a mixture of 23.4 g of the product of Step A and 230 ml of anhydrous ether and the mixture was stirred for 16 hours at room temperature and was poured over ice. The mixture was acidified with 200 ml of 2 N hydrochloric acid and was extracted 3 times with 250 ml of ether. The organic phase was washed 3 times with 100 ml of water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was taken up in 120 ml of petroleum ether (b.p.=60° to 80° C.) and the mixture was vacuum filtered. The product was dried to obtain 22.55 g of 5-cyclohexyl-2-hydroxy-α-methyl-α-phenyl-benzene-methanol melting at 119° C.

Workup

  1. additionwas poured over ice
  2. extractionwas extracted 3 times with 250 ml of ether
  3. washThe organic phase was washed 3 times with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. filtrationfiltered
  7. customThe product was dried

Sources & evidence

ORD record
ord-67c71698d676457f9af9162f9303608b
Source dataset
uspto-grants-1981_07
Patent number
US04281012

Reaction notes

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