Dimethylformamide → Methyl 4-(benzyloxy)benzoate

HRID 887395Notes

Reaction equation

HRID 887395 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.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 299810Methyl 4-(benzyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 2 L two-necked round bottom flask was charged methyl 4-hydroxybenzoate (100 g, 0.657 mol) and 500 mL of DMF. Potassium carbonate (180 g, 1.3 mol) was added and the mixture was cooled to 0° C. Benzylbromide (77 mL, 0.66 mol) was added dropwise to the reaction mixture with vigorous stirring for 30 min. After the addition was complete, the reaction mixture was stirred for 8 h at RT, then diluted with 500 ml water. The solid precipitated was collected by filtration and washed with water. Drying in a vacuum oven overnight provided the title compound.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for 8 h at RT
  3. customThe solid precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customDrying in a vacuum oven overnight

Sources & evidence

ORD record
ord-ae99f0ca91694edba4fa4ca614145008
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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