Methyl Acrylate → HCID 12273592, compound

HRID 1808229Notes

Reaction equation

HRID 1808229 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].[C:9]1(=[O:15])[CH2:14]CCC=[CH:10]1.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18].[Cl-].[NH4+]>C(OCC)C>[CH3:21][O:20][C:16]([CH:17]1[CH2:18][CH:14]2[CH2:7][CH2:5][CH:6]1[CH2:10][C:9]2=[O:15])=[O:19]

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 135942-Cyclohexen-1-oneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 12273592HCID 12273592, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a cooled (−3° C.) solution of lithiumdiisopropylamide (0.9 M in methylcyclohexane, 607 mL, 546 mmol, 1.05 eq) was added a solution of cyclohex-2-enone (52.6 g, 53 mL, 520 mmol, 1.0 eq) in diethyl ether (650 mL) over 90 min. During addition, the temperature was kept below −3° C. The mixture was stirred for an additional 25 minutes before a solution of methyl acrylate (46.8 mL, 520 mmol, 1.0 eq) in diethyl ether (450 mL) was added dropwise over 60 minutes. The temperature of the mixture was kept below 0° C. overnight. The mixture was poured out in saturated solution of ammonium chloride (1.0M) and stirred for 10 min. The sticky polymer was removed by filtration (P3). The organic layer was separated and the aqueous layer was extracted with tert-butyl methyl ether (2×300 mL). The combined organic layers were dried over sodium sulfate and concentrated. The title compound was isolated by distillation (0.001 mbar at 120-130° C.) and was isolated as a slightly yellow oil (39.8 g, 220 mmol, 42%).

Workup

  1. additionDuring addition
  2. customwas kept below −3° C
  3. additionwas added dropwise over 60 minutes
  4. customThe sticky polymer was removed by filtration (P3)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with tert-butyl methyl ether (2×300 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-73999c4951224b71b3b5214f37670bf1
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

Loading…