Sodium Iodide → HCID 58079476, compound

HRID 562538Notes

Reaction equation

HRID 562538 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(NC(C)C)(C)C.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1.[Na+].[I-]>CN1C(=O)CCC1.O>[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7912DiisopropylamineHCID 10459Hexadecanedioic acidHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 58079476HCID 58079476, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

Hexadecandioic acid (2 g, 7 mmol) was dissolved in dry NMP (25 mL). Diisopropylamin (1.2 mL, 7 mmol) and 4-methoxybenzyl chloride (0.95 mL, 7 mmol) was added, followed by NaI (0.52 g, 3.5 mmol). The mixture was heated to 80° C. for 1 hour, poured into water (100 mL) and filtered. The precipate was washed with dichloromethane (150 mL), the dichoromethane phase was dried (Na2SO4) and solvent removed in vacuo to yield the crude product, which was recrystallized several times from heptane to yield hexadecanedioic acid mono-(4-methoxy-benzyl)ester.

Workup

  1. filtrationfiltered
  2. washThe precipate was washed with dichloromethane (150 mL)
  3. dry with materialthe dichoromethane phase was dried (Na2SO4) and solvent
  4. customremoved in vacuo
  5. customto yield the crude product, which
  6. customwas recrystallized several times from heptane

Sources & evidence

ORD record
ord-a807c31c1f234a7f857bc3f17d56ec3f
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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