Benzyl Chloride → HCID 13275938, compound

HRID 2309109Notes

Reaction equation

HRID 2309109 reaction equation
[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg:9].[CH:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[C:11]1=O)[CH2:17]2>CCOCC>[CH2:11]([Mg:9][Cl:8])[C:10]1[CH:19]=[CH:14][CH:15]=[CH:16][CH:17]=1.[C:2]1([CH:1]=[C:11]2[CH:12]3[CH2:18][CH:16]4[CH2:15][CH:14]([CH2:19][CH:10]2[CH2:17]4)[CH2:13]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 64151AdamantanoneHCID 5462224Magnesium

Product 2

HCID 13275938HCID 13275938, compoundHCID 178418336HCID 178418336, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Benzylmagnesium chloride was prepared by reacting benzyl chloride (37.0 ml, 0.320 mol) with magnesium turnings (8.50 g, 0.350 mol) in 125 ml anhydrous ether (under N2). Then, a solution of 2-adamantanone (24.03 g, 0.160 mol) in 250 ml anhydrous ether was added gradually over a period of 60 minutes. The resulting suspension was stirred at room temperature for 18 hours, and then quenched by cautious addition of 250 ml 2N hydrochloric acid. The organic layer was separated, washed with water, then dried over MgSO4, and the solvent evaporated leaving, after crystallization from pentane, 32.47 g (84%) of 2-(phenylmethyl)-tricyclo[3.3.1.13,7 ]-decan-2-ol. Mp 58°-60° C. The decanol compound was then dehydrated using the method of Keul1 to produce 2-(phenyl-methylene)-tricyclo[3.3.1.13,7 ]decane. The dehydration procedure was as follows:

Workup

  1. customquenched by cautious addition of 250 ml 2N hydrochloric acid
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent evaporated
  6. customleaving
  7. customafter crystallization from pentane, 32.47 g (84%) of 2-(phenylmethyl)-tricyclo[3.3.1.13,7 ]-decan-2-ol

Sources & evidence

ORD record
ord-076458ec6a7946e18e7c110fa3a68b00
Source dataset
uspto-grants-1987_09
Patent number
US04692515

Reaction notes

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