Hydroxide → HCID 18319079, compound

HRID 1700948Notes

Reaction equation

HRID 1700948 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:6][CH:5]=1.[K].[OH-]>C(O)C.O>[CH2:14]([S:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][CH:6]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 961HydroxideHCID 5462222PotassiumHCID 22949962HCID 22949962, compound

Product 1

HCID 18319079HCID 18319079, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-[2-(dodecylthio)ethoxy]benzoic acid methyl ester (11.29 g, 29.7 mmol) in 80% aqueous ethanol (100 ml) was treated with a solution of potassium, hydroxide, (6.0 g, 0.107 mol) in water (15 ml) and the resulting mixture was heated at 80° C. for 2 h. The solvent was then concentrated in vacuo and the residue was treated with 150 ml of 1N aqueous hydrochloric acid. The aqueous phase was extracted three times with dichloromethane and the combined organic extracts were washed with brine, dried (magnesium sulfate) and evaporated. The residue was recrystallized from dichloromethane to give 10.24 g (94%) of the title material as white needles: mp 97-98° C.

Workup

  1. concentrationThe solvent was then concentrated in vacuo
  2. additionthe residue was treated with 150 ml of 1N aqueous hydrochloric acid
  3. extractionThe aqueous phase was extracted three times with dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-f92339c648fb46a185fdfc7c08172e83
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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