Hydrochloric Acid → 4-(Tetradecyloxy)benzoic acid

HRID 247912

Reaction equation

HRID 247912 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. MP 94°-96° C.

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-1f1a5e5e33ab43668325737b19d38676
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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