Phenol → Phenyl heptanoate

HRID 485627Notes

Reaction equation

HRID 485627 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:10]1(O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.S(=O)(=O)(O)O>>[C:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 8094Heptanoic Acid

Product 1

HCID 521712Phenyl heptanoate

Conditions

Temperature
131 °C

Procedure

Heptanoic acid (180.9 g; 1.39 mol), phenol (180.69 g; 1.92 mol), toluene (216.5; 2.35 mol) and sulfuric acid (5.04 g; 0.0514 mol) were charged to a 2-liter, 3-necked round bottom flask equipped with a thermometer, a magnetic stirrer and an 8" Vigreux column equipped with a Dean-Stark trap. The reaction mixture was heated to 131° C. and maintained at that temperature for five hours to give 74 weight percent phenyl heptanoate. The reaction product was washed once with a solution of 0.08 mol Na2CO3 in 4.5 mol water. Phase separation occurred after approximately 20 minutes. The organic layer was fractionally distilled at atmospheric pressure using a 20-plate Oldershaw column to remove phenol and toluene. The remaining liquid was then distilled through a 10-plate Oldershaw column at 50 torr to give a center cut fraction of 154.4 g (54% yield) of pure phenyl heptanoate.

Workup

  1. customequipped with a thermometer, a magnetic stirrer
  2. customan 8" Vigreux column equipped with a Dean-Stark trap
  3. temperaturemaintained at that temperature for five hours

Sources & evidence

ORD record
ord-4f49cb49b1e44efb8171a114cffa4019
Source dataset
uspto-grants-1985_08
Patent number
US04537724

Reaction notes

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