Dichloromethane → Methyl 2-cyclohexylideneacetate

HRID 555972Notes

Reaction equation

HRID 555972 reaction equation
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])[CH3:3].[H-].[Na+].[C:14]1(=O)[CH2:19][CH2:18]C[CH2:16][CH2:15]1.[CH2:21](Cl)Cl>>[C:3]1(=[CH:2][C:4]([O:6][CH3:21])=[O:5])[CH2:18][CH2:19][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7967CyclohexanoneHCID 24758Sodium hydrideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 11126470Methyl 2-cyclohexylideneacetate

Procedure

2.184 g trimethylphosphonoacetate was dissolved in DCM, stirred on ice-water bath, and 384 mg NaH was added. After 6 hours 980 mg cyclohexanone was added into the reaction flask, and stirred at ambient temperature overnight. The next day, the reaction mixture was washed with water twice, saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours, filtrated, and the filtrate was dried under vacuum to give 1.227 g of the title crude product.

Workup

  1. stirringstirred at ambient temperature overnight
  2. washThe next day, the reaction mixture was washed with water twice
  3. dry with materialsaturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours
  4. filtrationfiltrated
  5. customthe filtrate was dried under vacuum

Sources & evidence

ORD record
ord-f76a76ee8b7e4a0f902410379605ac65
Source dataset
uspto-grants-2011_11
Patent number
US08053577B2

Reaction notes

Loading…