Pyridine → 1,2-Benzenedimethanol

HRID 525638

Reaction equation

HRID 525638 reaction equation
[C:1]1(CO)[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.ClCCl.[C:20](Cl)(=[O:24])C(C)C>CN(C1C=CN=CC=1)C.[Cl-].[Na+].O>[C:3]1([CH2:20][OH:24])[C:4]([CH2:7][OH:8])=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 115061,4-BenzenedimethanolHCID 62325Isobutyryl chloride

Product 1

HCID 691531,2-BenzenedimethanolYield 212.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

1,4-xylylene glycol (5 g, 0.0306 mol), pyridine (5.7 g, 0.072 mol), and catalyst DMAP (ca. 100 mg) in a solution of dichloromethane (ca. 25 ml) were added to a flask. Isobutyryl chloride (7.71 g, 0.072 mol) was then added to the solution drop wise. The mixture was stirred overnight. 1M HCL brine was used to wash the mixture. The organic layer was dried over MgSO4 and concentrated in vacuo to afford a clear oil as the product (9 g). Its purity was ascertained using 1H NMR (300 MHz in CDCL3): δ 7.34 (s, 4H), 5.11 (s, 4H), 2.60 (sept, 2H), 1.19 (d, 12H).

Workup

  1. washto wash the mixture
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-709dbd25a92f41c0adc014e5dfe877dd
Source dataset
uspto-grants-2016_05
Patent number
US09340658B2

Linked notes

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