Sodium Iodide → HCID 58079476, compound

HRID 444998

Reaction equation

HRID 444998 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 recrystalized 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 recrystalized several times from heptane

Sources & evidence

ORD record
ord-d56b3bbfe0984fc58760dd7d3d47ace5
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Linked notes

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