1,4-Benzenedimethanol → HCID 68811474, compound

HRID 898192Notes

Reaction equation

HRID 898192 reaction equation
[H-].[Na+].[C:3]1([CH2:11][OH:12])[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.I[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C1COCC1>[CH2:14]([O:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:11][OH:12])=[CH:4][CH:5]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 115061,4-BenzenedimethanolHCID 123801-IodooctaneHCID 24758Sodium hydride

Product 1

HCID 68811474HCID 68811474, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.17 g, 7.20 mmol) was added to a solution of 1,4-benzene dimethanol (1.00 g, 7.20 mmol) in THF at 0° C. The reaction was stirred for 1 h. 1-iodooctane (1.73 g; 7.20 mmol) was added and the reaction mixture was warmed to rt for 4 h and then heated at 50° C. for 2 days. The reaction was cooled and filtered. Silica gel chromatography eluting with 15% ethyl acetate/hexane gave 0.14 g of product: 1H NMR (500 MHz) δ 7.34-7.40 (m, 4H), 4.68-4.72 (m, 2H, 4.51 (s, 2H), 3.46-3.50 (m, 2H), 1.61-1.68 (m, 2H), 1.24-1.40 (m, 10H), 0.88-0.92 (m, 3H).

Workup

  1. temperatureheated at 50° C. for 2 days
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. washSilica gel chromatography eluting with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e3499614f7534c57a86623effbfbc22c
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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