Benzoic Acid → Benzyl Benzoate

HRID 1761270Notes

Reaction equation

HRID 1761270 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC1C=C(OC)C=CC=1>O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[C:1]([O:9][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 7503Benzyl ChlorideHCID 75303-MethoxytolueneHCID 14798Sodium Hydroxide

Product 1

HCID 2345Benzyl Benzoate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

A mixture comprising benzoic acid (2.45 g, 20 millimoles, Aldrich, 99%), sodium hydroxide (1.90 g, 22.5 millimoles, 50% w/w solution in water, Aldrich) and water (247.2 g) was stirred magnetically at room temperature for about two hours until the solids dissolved in water. The excess molar concentration of sodium hydroxide was 0.125. Next, the aqueous phase was transferred to a three-necked 500 mL flask and warmed up to 45° C. The organic phase consisting of benzyl chloride (7.60 g, 60 millimoles, Aldrich, 97%), 3-methylanisole (GC standard, 0.616 g, 5 millimoles, Aldrich, 99%), and Adogen 464 (0.905 g, 2 millimoles, Aldrich) was added to the aqueous phase and the two phase system was stirred mechanically (600 rpm, a calibrated photo-tachometer) for three hours at 45° C. The organic phase:aqueous phase weight ratio was 1:27. The aliquot, taken after 180 minutes after the addition of the organic phase, was briefly centrifuged, the phases were separated and the organic phase was injected into the GC instrument. The yield of benzyl benzoate based on the limiting reactant (benzoic acid) was 87%. Benzyl Benzoate was accompanied by a small quantity of benzyl alcohol (less than 5%).

Workup

  1. concentrationThe excess molar concentration of sodium hydroxide
  2. customNext, the aqueous phase was transferred to a three-necked 500 mL flask
  3. additionwas added to the aqueous phase
  4. waitThe aliquot, taken after 180 minutes
  5. additionafter the addition of the organic phase
  6. customthe phases were separated

Sources & evidence

ORD record
ord-8ce13b47cf594424ae971e9e20aae5e2
Source dataset
uspto-grants-2005_01
Patent number
US06846946B2

Reaction notes

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