Methylparaben → HCID 54475829, compound

HRID 363041Notes

Reaction equation

HRID 363041 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:18]1([CH2:24]Br)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C=O)C>[CH:18]1([CH2:24][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 54475829HCID 54475829, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-hydroxybenzoate 23-1 (24.3 g, 160 mmol) in 250 mL of DMF was added 62 g (190 mmol) of Cs2CO3 followed by 20.4 mL (146 mmol) of cyclohexylmethyl bromide. The resulting slurry was then heated at 50° C. for 20 h. The solvent was distilled under reduced pressure and the residue was taken up in 500 mL of EtOAc. The organic phase was extracted with 1N NaOH (2×150 mL), water (5×150 mL) and brine (150 mL), dried (MgSO4) and concentrated to afford product 23-2 as a white solid.

Workup

  1. distillationThe solvent was distilled under reduced pressure
  2. extractionThe organic phase was extracted with 1N NaOH (2×150 mL), water (5×150 mL) and brine (150 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b791bfe080f444279b790a38436b3560
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

Loading…