Hydrochloric Acid → 4'-(cis-9-Octadecenyloxy)-4-biphenylcarboxylic acid

HRID 369530Notes

Reaction equation

HRID 369530 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].O.[OH-].[Li+].Cl>O>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70012153Methyl-4'-(cis-9-octadecenyloxy)-4-biphenylcarboxylate

Product 1

HCID 700113904'-(cis-9-Octadecenyloxy)-4-biphenylcarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Water (approximately 15 ml) was added to a solution of ester 28b (486 mg, 1.00 mmol) in 50 ml of an 80/20 (v/v) (methanol/THF) solution, until it remained milky white with vigorous stirring. To this suspension was added lithium hydroxide monohydrate (213 mg, 5.1 mmol), the reaction mixture was refluxed overnight and then was acidified with concentrated HCl. Water (approximately 20 ml) was added and the solution was cooled, filtered, washed several times with water, and air dried, yielding 422 mg (89%) of a white waxy powder.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperaturethe solution was cooled
  3. filtrationfiltered
  4. washwashed several times with water, and air
  5. customdried
  6. customyielding 422 mg (89%) of a white waxy powder

Sources & evidence

ORD record
ord-c77c6d7909a44cbab699bfe21944a6bd
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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