Hydrochloric Acid → p-n-Octadecyloxybenzoic acid

HRID 413633

Reaction equation

HRID 413633 reaction equation
C[O:2][C:3](=[O:29])[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][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:6][CH:5]=1.CO.O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:29])=[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][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 4189536Methyl 4-(octadecyloxy)benzoate

Product 1

HCID 139993p-n-Octadecyloxybenzoic acidYield 71.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester 35a (405 mg, 1.0 mmol) was dissolved in 15 ml THF and 50 ml methanol was added. Water (approximately 10 ml) was added until the solution remained cloudy with vigorous stirring, at which time lithium hydroxide monohydrate (840 mg, 20.0 mmol) was added. The reaction mixture was refluxed overnight, acidified with concentrated HCl and cooled. The precipitate was filtered, washed with water and air dried to yield 279 mg (71%) of a white powder.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed overnight
  3. temperaturecooled
  4. filtrationThe precipitate was filtered
  5. washwashed with water and air
  6. customdried

Sources & evidence

ORD record
ord-95cbca864e344aa39a980a29ffce107d
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Linked notes

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