Ethanol → 4-(Tetradecyloxy)benzoic acid

HRID 2119139Notes

Reaction equation

HRID 2119139 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH-:26].[Na+].O.[CH2:29]([OH:31])C>>[CH2:11]([O:10][C:5]1[CH:4]=[CH:9][C:8]([C:29]([OH:31])=[O:26])=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 12361482HCID 12361482, compound

Product 1

HCID 2894104-(Tetradecyloxy)benzoic acid

Procedure

Twenty grams of tetradecyloxy benzoic acid methyl ester and 2.75 g of sodium hydroxide were dissolved in 80 ml of ethanol. After the addition of 50 ml of water was heated for 2.5 hours to boiling temperature. The resulting suspension was concentrated by evaporation and the evaporation residue was dissolved in hot water. The solution then was acidified with dilute hydrochloric acid, filtered, washed with water and dried. 4-tetradecyloxybenzoic acid melting at 95° to 99° C. (clear at 135° C. was obtained in a yield of 18.2 g, corresponding to 95% of the theoretical.

Workup

  1. temperaturewas heated for 2.5 hours
  2. concentrationThe resulting suspension was concentrated by evaporation
  3. dissolutionthe evaporation residue was dissolved in hot water
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-689aa8dad33141b6868914703940d2be
Source dataset
uspto-grants-1987_07
Patent number
US04683244

Reaction notes

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