Sodium Hydroxide → HCID 380443, compound

HRID 1989842Notes

Reaction equation

HRID 1989842 reaction equation
[I:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58773804Methyl 11-(4-iodophenoxy)undecanoate

Product 1

HCID 380443HCID 380443, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 11-(4-iodophenoxy)undecanoate (10 g, 23.9 mmmol), in methanol (100 ml) was treated with sodium hydroxide (2.4 g, 60 mmol). The stirred reaction was heated at 40 C for 60 h. The reaction contained a heavy white precipitate at the end of the reaction. The reaction was then cooled to room temperature and concentrated in vacuo. The resulting solid was then treated with 1N hydrochloric acid (250 ml) and ethyl acetate (250 ml) and stirred vigorously until the solid had dissolved. The organic phase was separated dried over sodium sulfate and concentrated in vacuo to give 11-(4-iodophenoxy)-undecanoic acid (9.55 g, 23.6 mmol, 98%) δH (CDCl3)1.29-1.78 (16H, m, 3,4,5,6,7,8,9,10-CH2), 2.35 (2H, t, 2-CH2), 3.90 (2H, t, 11-CH2), 6.66 (2H, dd, 2,6-ArH), 7.53 (2H, dd, 3,5,-ArH), δc(CDCl3) 24.61, 25.92, 28.98, 29.08, 29.16, 29.27, 29.41, 34.02, 68.08, 82.37, 116.90, 138.11, 158.97, and 180.18.

Workup

  1. customThe stirred reaction
  2. temperaturewas heated at 40 C for 60 h
  3. customat the end of the reaction
  4. concentrationconcentrated in vacuo
  5. additionThe resulting solid was then treated with 1N hydrochloric acid (250 ml) and ethyl acetate (250 ml)
  6. dissolutionhad dissolved
  7. customThe organic phase was separated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0474d2dcee64db4a7e6882891ca86e5
Source dataset
uspto-grants-2010_01
Patent number
US07642373B2

Reaction notes

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