Methylparaben → Methyl 4-(t-butyloxyacetyloxy)benzoate

HRID 1599937Notes

Reaction equation

HRID 1599937 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=O.[OH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.C([O-])([O-])=[O:22].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[C:6]([O:5][CH2:3][C:2]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)=[O:22])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 18928531Methyl 4-(t-butyloxyacetyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

t-Butyl bromoacetate (0.83 mL, 5.1 mmol), methyl 4-hydroxybenzoate (780 mg, 5.1 mmol) and Cs2CO3 (1.83 g, 5.6 mmol) were combined in 25 mL DMF. After 16 h, the reaction was diluted with ethyl acetate, washed with water, saturated NaHCO3, 10% KHSO4 and brine, dried (MgSO4) and concentrated providing 24-1 as a yellow oil. Rf 0.84 (silica, 50% EtOAC/hexane).

Workup

  1. washwashed with water, saturated NaHCO3, 10% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-67f65865393a4693a7fca6acffb3ae37
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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