Ethanol → 4-(Tetradecyloxy)benzoic acid

HRID 484590

Reaction equation

HRID 484590 reaction equation
[CH2:1]([O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=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][CH3:14].[OH-].[K+].CO.C(O)C>O>[CH2:1]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=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][CH3:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 14797Potassium HydroxideHCID 3312490Methyl 4-(tetradecyloxy)benzoate

Product 1

HCID 2894104-(Tetradecyloxy)benzoic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 120 g of methyl p-(tetradecyloxy)benzoate, 57.96 g of potassium hydroxide, 1-liter of methyl alcohol, 400 ml of ethyl alcohol and 60 ml of water is refluxed for 4.5 hours. A solid is formed and the reaction mixture partitioned between dilute hydrochloric acid and chloroform with some warming. The organic layer is washed with warm dilute hydrochloric acid and dried. The filtrate is evaporated to a volume of 600 ml and an equal volume of hexanes added to form a solid which is dried to give 104 g of the desired product as a white solid, m.p. 94°-96° C.

Workup

  1. temperatureis refluxed for 4.5 hours
  2. customA solid is formed
  3. customthe reaction mixture partitioned between dilute hydrochloric acid and chloroform with some warming
  4. washThe organic layer is washed
  5. temperaturewith warm dilute hydrochloric acid
  6. customdried
  7. customThe filtrate is evaporated to a volume of 600 ml
  8. additionan equal volume of hexanes added
  9. customto form a solid which
  10. customis dried

Sources & evidence

ORD record
ord-265f1d19381348fa8eb25d6b787c84c1
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Linked notes

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