Ethanol → 4-(Tetradecyloxy)benzoic acid

HRID 1762447Notes

Reaction equation

HRID 1762447 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

20 g tetradecyloxybenzoic acid methyl ester were dissolved with 2.75 g sodium hydroxide in 80 ml ethanol and, after addition of 50 ml water, the resulting solution was heated for 2.5 hours to boiling temperature. After the suspension was concentrated by evaporation, the residue was dissolved in hot water and the resulting solution acidified with dilute acid. 18.2 g (95% of the theoretical) 4-tetradecyloxybenzoic acid melting at 95° to 99° C. (clear at 135° C.) were obtained after filtering, washing with water, and drying.

Workup

  1. temperaturethe resulting solution was heated for 2.5 hours
  2. concentrationAfter the suspension was concentrated by evaporation
  3. dissolutionthe residue was dissolved in hot water
  4. additionwith dilute acid

Sources & evidence

ORD record
ord-eb58dfcbd7d345b5b4b287d07fe58f4a
Source dataset
uspto-grants-1989_05
Patent number
US04833147

Reaction notes

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