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

HRID 413636
Notes
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Reaction equation

HRID 413636 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent

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-7c7bfaec688b497ab1763a6e6844ba58
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06569504B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes