Hydrochloric Acid → 2,2-Bis(6-benzyloxyhexyl)acetic acid

HRID 1289384Notes

Reaction equation

HRID 1289384 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]([O:18]CC)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO>[CH2:28]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]([OH:18])=[O:17])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18920832Ethyl 2,2-bis(6-benzyloxyhexyl)acetate

Product 1

HCID 189208392,2-Bis(6-benzyloxyhexyl)acetic acidYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

First, 12 g of ethyl 2,2-bis(6-benzyloxyhexyl)acetate, 250 ml of methanol, and 100 ml of an aqueous solution containing 16.8 g of 85% potassium hydroxide were placed in a 500 ml flask. Then, the mixture was stirred under reflux for 2 hours. The reaction mixture was poured into diluted hydrochloric acid, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was recrystallized from a mixed solvent of hexane and acetone to obtain 6.2 g of 2,2-bis(6-benzyloxyhexyl)acetic acid (Y: 55%).

Workup

  1. customwere placed in a 500 ml flask
  2. temperatureunder reflux for 2 hours
  3. extractionan organic layer was extracted with ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled away
  7. customThe residue was recrystallized from a mixed solvent of hexane and acetone

Sources & evidence

ORD record
ord-b8cb1134b8f24782907061084f72bf38
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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