Water → Benzyl 5-(benzyloxy)-2-methylbenzoate

HRID 709685Notes

Reaction equation

HRID 709685 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:11][C:5]1[CH:6]=[CH:10][CH:2]=[CH:3][CH:4]=1)=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2351885-Hydroxy-2-methylbenzoic acid

Product 1

HCID 67363220Benzyl 5-(benzyloxy)-2-methylbenzoateYield 168.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-2-methylbenzoic acid (1.52 g) in DMF (25 mL) were added benzyl bromide (3.40 g) and potassium carbonate (4.14 g), and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration, and dried to give the title compound (2.80 g) as a white solid. This compound was used for the next step without further purification.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-2ce41ea520d545f483b602fac6928391
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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