Hydrochloric Acid → 4-(Tetradecyloxy)benzoic acid

HRID 1728789Notes

Reaction equation

HRID 1728789 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([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])=[CH:6][CH:5]=1.[OH-].[K+].Cl>C(Cl)Cl.O.CO.C(O)C>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:25])=[O:2])=[CH:9][CH:8]=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

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 3312490Methyl 4-(tetradecyloxy)benzoate

Product 1

HCID 2894104-(Tetradecyloxy)benzoic acidYield 99%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 20 g of product from Example 1 is added 9.66 g potassium hydroxide, 160 ml methyl alcohol, 10 ml water and 70 ml ethyl alcohol. The reaction mixture is refluxed for 6.5 hours, during which time an additional 100 ml methyl alcohol and 100 ml water is added. To the cooled reaction mixture is added 1 L of methylene chloride and sufficient concentrated hydrochloric acid to make the reaction pH acidic. The white crystals are collected and dried in vacuo over phosphorus pentoxide to give 19.0 g of the desired product.

Workup

  1. additionis added
  2. customTo the cooled reaction mixture
  3. customThe white crystals are collected
  4. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-adcb4341c39e4907bde38f98c494dc31
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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