Iodine → 1-Iodotetratriacontane

HRID 1902815Notes

Reaction equation

HRID 1902815 reaction equation
O1CCCC1.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[I:40]I.[I-]>C1C=CC=CC=1>[CH2:6]([I:40])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 807IodineHCID 8028TetrahydrofuranHCID 30165Iodide Ion2×HCID 53788575Tetratriacont-17-ene

Product 1

HCID 126961461-Iodotetratriacontane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 44.8 g. (0.15 mole) of Cp2ZrCl2 in 800 ml. tetrahydrofuran under Argon was added 24.7 g. (0.086 mole) of NaAlH2 (OCH2CH2OCH3)2 in benzene via syringe. After stirring 2 hours at room temperature, 36.8 g. (0.077 mole) of the olefin, 17-tetratriacontene, was added and the mixture kept at 40° C. for 7 days. After cooling in an ice bath, solid iodine (34.0 g., 0.134 mole) was added. The mixture was filtered and the solvent removed in vacuum. NMR analysis indicated an olefin:iodide ratio of 25:75. The residue was dissolved in hexane and percolated through dry silica gel to remove impurities. Recrystallization from hexane gave 13.0 g. pure iodide, m.p. 75°-6° C. and 14.4 g. of a 58:42 olefin:iodide mixture.

Workup

  1. waitthe mixture kept at 40° C. for 7 days
  2. temperatureAfter cooling in an ice bath
  3. filtrationThe mixture was filtered
  4. customthe solvent removed in vacuum
  5. dissolutionThe residue was dissolved in hexane
  6. customto remove impurities
  7. customRecrystallization from hexane
  8. customgave 13.0 g

Sources & evidence

ORD record
ord-4de8f22f011d4a848e20bda47788e158
Source dataset
uspto-grants-1982_12
Patent number
US04366101

Reaction notes

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