Toluene → HCID 72460980, compound

HRID 1296854Notes

Reaction equation

HRID 1296854 reaction equation
C([O:3][C:4](=O)[C:5]([CH3:27])=[CH:6][CH:7]=[CH:8][C:9]([CH3:26])=[CH:10][CH:11]=[CH:12][CH:13]=[C:14]([CH3:25])[CH:15]=[CH:16][CH:17]=[C:18]([CH3:24])[C:19](OCC)=[O:20])C.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl.O>[CH3:24][C:18](=[CH:17][CH:16]=[CH:15][C:14]([CH3:25])=[CH:13][CH:12]=[CH:11][CH:10]=[C:9]([CH3:26])[CH:8]=[CH:7][CH:6]=[C:5]([CH3:27])[CH2:4][OH:3])[CH2:19][OH:20]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 73069762HCID 73069762, compound

Product 1

HCID 72460980HCID 72460980, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6,11,15-tetramethyl-hexadeca-2,4,6,8,10,12,14-heptaenedioic acid diethyl ester (200 g, 0.52 mol) in 3000 mL of DCM was added dropwise a solution of diisobutylaluminum hydride in toluene (1.5 M, 1533 mL, 2.30 mol) at −78° C. The mixture was stirring at 0° C. for 2 h. 100 mL of water was added the 200 ml of 2N NaOH was added to quench the reaction. The suspension was filtered off and solid was washed by a large amount of THF. The combined organic layer were dried over Na2SO4 and evaporated to give 133.16 g (85%) brown solid. 1H NMR (300 Hz, CDCl3) δ 6.41 (m, 10H, CH), 4.16 (s, 4H, CH2), 1.95 (m, 12H, CH3).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. filtrationThe suspension was filtered off
  5. washsolid was washed by a large amount of THF
  6. dry with materialThe combined organic layer were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-443e8adb39394a328c1e3e6d9360284b
Source dataset
uspto-grants-2007_07
Patent number
US07247752B2

Reaction notes

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