Benzoic Acid → Behenyl Benzoate

HRID 414170Notes

Reaction equation

HRID 414170 reaction equation
[CH2:1]([OH:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:24](O)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:24]([O:23][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 12620Behenyl Alcohol

Product 1

HCID 3025489Behenyl Benzoate

Conditions

Temperature
100 °C

Procedure

A mixture of 106.5 gms. (0.326 moles) of behenyl alcohol, 43.5 gms. (0.343 moles) of benzoic acid and 225 mgms. stannous oxalate was heated to 230° C. under nitrogen. The reaction was held at 230° C. for two hours, and the distillate collected. It was then cooled to 100° C. The acidity was 10.0 mg KOH/gm. The ester was then given a treatment for 30 minutes at 85° C. with 50 gms. deionized water, 2 gms. sodium carbonate, 2 gms. sodium chloride, and 1 gm. hydrogen peroxide. It was then allowed to stand and the lower aqueous layer drained off. The top layer was washed with 50 gms. water at 80°-85° C. and then separated. The solid was then vacuum stripped at 100°-105° C. to remove residual moisture. The final product was a solid benzoate ester having the following formula: ##STR14##

Workup

  1. additionA mixture of 106.5 gms
  2. distillationthe distillate collected
  3. customfor 30 minutes
  4. customat 85° C.
  5. washThe top layer was washed with 50 gms
  6. customwater at 80°-85° C. and then separated
  7. customstripped at 100°-105° C.
  8. customto remove residual moisture

Sources & evidence

ORD record
ord-6e1dfd46f81b43029b7b635cee379982
Source dataset
uspto-grants-1988_12
Patent number
US04791097

Reaction notes

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