Hydrochloric Acid → 4-(trans-4-Decenyloxy)-benzoic acid

HRID 369539Notes

Reaction equation

HRID 369539 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1.O.O.[OH-].[Li+].Cl>CO>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:21])=[O:2])=[CH:9][CH:8]=1)[CH2:12][CH2:13]/[CH:14]=[CH:15]/[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 18521044Methyl-4-(trans-4-decenyloxy)-benzoate

Product 1

HCID 185210594-(trans-4-Decenyloxy)-benzoic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester 35i (500 mg, 1.7 mmol) was dissolved in 50 ml methanol. Water (approximately 10 ml) was added until the solution remained cloudy, at which time lithium hydroxide monohydrate (723 mg, 17.0 mmol) was added. The reaction mixture was refluxed overnight and acidified with concentrated HCl. Water was added (approximately 30 ml), the mixture was cooled, filtered, washed with water and allowed to air dry yielding 400 mg (84%) of a white powder.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed overnight
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. washwashed with water
  6. customto air dry

Sources & evidence

ORD record
ord-da62695761de4d9db9c706e6c545204f
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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