Hydrochloric Acid → 4,4'-(Cyclopenta-2,4-dien-1-ylidenemethylene)bis(methylbenzene)

HRID 1174075Notes

Reaction equation

HRID 1174075 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.O1[CH2:21][CH2:20][CH2:19][CH2:18]1.Cl.[CH2:23](OCC)C>>[C:11]1([CH3:14])[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([CH3:1])=[CH:3][CH:4]=2)=[C:18]2[CH:23]=[CH:21][CH:20]=[CH:19]2)=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 691484,4'-Dimethylbenzophenone

Product 1

HCID 124276304,4'-(Cyclopenta-2,4-dien-1-ylidenemethylene)bis(methylbenzene)Yield 74.5%

Procedure

To a 200-ml two-neck flask equipped with a magnetic stirrer, a three-way cock, 6.72 g (31.9 mmol) of 4,4′-dimethylbenzophenone, and 30 ml of tetrahydrofuran were charged under nitrogen atmosphere. 19 ml (38 mmol) of a 2.0 mol/l sodium cyclopentadienyl/tetrahydrofuran solution was gradually added thereto, while cooling it in an ice water bath, and the mixture was stirred at room temperature for 6 days. 100 ml of 1 N hydrochloric acid was gradually added thereto, while cooling it in an ice water bath and 100 ml of diethyl ether was added. The organic layer was separated, and washed twice with 100 ml of water, and once with 100 ml of saturated solution of salt. After the solution was dried over magnesium sulfate, the solvent was distilled off, and the obtained product was purified by column chromatography. The production quantity was 6.15 g, and the yield was 74.5%. Identification was performed by 1H NMR spectrum. The measurement result is shown as follows.

Workup

  1. customTo a 200-ml two-neck flask equipped with a magnetic stirrer
  2. temperaturewhile cooling it in an ice water bath
  3. temperaturewhile cooling it in an ice water bath
  4. customThe organic layer was separated
  5. washwashed twice with 100 ml of water
  6. dry with materialAfter the solution was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customthe obtained product was purified by column chromatography
  9. customThe measurement result

Sources & evidence

ORD record
ord-c13ca2f3d606449c8faf509cbc0382f1
Source dataset
uspto-grants-2010_11
Patent number
US07834204B2

Reaction notes

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