Diethyl Ether → HCID 10942917, compound

HRID 231933Notes

Reaction equation

HRID 231933 reaction equation
CCO[CH2:4][CH3:5].[C:6]1([CH:12]2[CH2:17][CH2:16]C(=O)[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[C:6]1([CH:12]2[CH2:17][CH2:16][C:4](=[CH2:5])[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 786054-Phenylcyclohexanone

Product 1

HCID 10942917HCID 10942917, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BDAM (3.00 grams) was suspended in 30 milliliters of dry CH2Cl2. Two molar equivalents of ether were added dropwise to the chilled suspension. After about 10 minutes of stirring, a homogeneous solution was formed. At this point, 1 molar equivalent of TMAL (1.1 milliliter) was added. The reaction mixture was stirred at room temperature for 15 minutes and 2.00 grams of 4-phenylcyclohexanone were added. Vigorous reflux which quickly subsided was noticed. The reaction mixture was stirred at room temperature for 3 hours and hydrolyzed as described in Example 1. The aqueous layer was acidified to help separate the organic layer. After the usual work up and column separation, 1.75 grams of 4-phenyl-1-methylenecyclohexane were isolated (88% yield).

Workup

  1. customa homogeneous solution was formed
  2. additionAt this point, 1 molar equivalent of TMAL (1.1 milliliter) was added
  3. stirringThe reaction mixture was stirred at room temperature for 15 minutes
  4. temperatureVigorous reflux which
  5. stirringThe reaction mixture was stirred at room temperature for 3 hours
  6. customto help separate the organic layer
  7. customAfter the usual work up and column separation

Sources & evidence

ORD record
ord-97228aecdc0a46d09e91ad23ff7a33e4
Source dataset
uspto-grants-1989_07
Patent number
US04849574

Reaction notes

Loading…