Benzoic Acid → Arachidyl benzoate

HRID 414169Notes

Reaction equation

HRID 414169 reaction equation
[CH2:1]([OH:21])[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][CH3:20].[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[K+]>>[CH2:1]([O:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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][CH3:20]

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 124041-EicosanolHCID 14797Potassium Hydroxide

Product 1

HCID 15607780Arachidyl benzoate

Conditions

Temperature
100 °C

Procedure

A mixture of 104 gms. (0.348 moles) of arachidyl alcohol, 46 gms. (0.362 moles) of benzoic acid and 225 mgms. stannous oxalate was heated under nitrogen to 230° C. The reaction was held at 230° C. for two hours under nitrogen. The acidity was 10 mgms. KOH/gms. The mixture was then cooled to 100° C. During the reaction distillate was collected. The ester formed was solid at room temperature and showed solidication at 80° C. The ester was given a treatment at 85° C. with 50 gms. deionized water containing 2 gms. sodium carbonate, 2 gms. sodium chloride and 1 gm. hydrogen peroxide. The mixture was allowed to stand and separate. The top layer was washed with 50 gms. deionized water at 80°-85° C., separated and cooled. The top layer solidified and bottom layer was completely drained off. The ester was then vacuum stripped at 100°-105° C. The ester so formed was a white solid benzoate.

Workup

  1. additionA mixture of 104 gms
  2. distillationDuring the reaction distillate was collected

Sources & evidence

ORD record
ord-7091a72ada0842538e2c6bae092b4e17
Source dataset
uspto-grants-1988_12
Patent number
US04791097

Reaction notes

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