Hydrochloric Acid → [4-(Hexadecyloxy)phenoxy]acetic acid

HRID 484611Notes

Reaction equation

HRID 484611 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:8][CH:7]=1.[OH-].[K+].Cl>O.C(O)C>[CH2:13]([O:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:11][CH:10]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 102507944-Hexadecyloxyphenoxyacetic acid methyl ester

Product 1

HCID 9977851[4-(Hexadecyloxy)phenoxy]acetic acidYield 57.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 24.5 g of 4-Hexadecyloxyphenoxyacetic acid methyl ester 10.14 g of potassium hydroxide in 10 ml of water and 250 ml ethyl alcohol is refluxed for 3 hours then allowed to stand at 50° for 18 hours. The mixture is poured into dilute hydrochloric acid and extracted with chloroform. The organic layer is evaporated to a residue which is crystallized from hexane:carbon tetrachloride to give 13.7 g of the desired product as a white solid, m.p. 125°-127° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. extractionextracted with chloroform
  3. customThe organic layer is evaporated to a residue which
  4. customis crystallized from hexane

Sources & evidence

ORD record
ord-d942a343e5634fe5ad42e8e40abfb43c
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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