Pyridine → HCID 23437329, compound

HRID 2120021Notes

Reaction equation

HRID 2120021 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C=CC=CC=1>ClCCl>[C:1]([O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 124137162-(Hexyloxy)phenol

Product 1

HCID 23437329HCID 23437329, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.4 g, 30.1 mmol) was added dropwise to vigorously stirred mixture of 2-hexyloxyphenol (5.0 g, 25.8 mmol) and pyridine (5 ml) in dichloromethane (50 ml). The mixture was stirred for 1 hour and poured onto water. The organic layer was separated, dried (MgSO4), concentrated to give crude product which was purified by column chromatography on silica gel using dichloromethane petroleum spirit (1:3) as eluent to give title compound as a colourless oil (5.78 g, 95%). Found: C, 71.00; H, 8.35. C14H20O3 requires C, 71.19; H, 8.47. δH (CHCl3) 7.21-7.15 (m, 1H, ArH), 7.05-7.01 (m, 1H, ArH), 6.97-6.89 (m, 2H, ArH), 3.97 (t, J 6.5, 2H, OCH2), 2.30 (s, 3H, COCH3), 1.78-1.71 (m, 2H, ArOCH2CH2), 1.57-1.30 (m, 6H, CH2), 0.90 (t, J 6.9, 3H, CH2CH3). MS (FAB), 236 (M+, 53%), 194 (100%), 153 (27%), 110 (34%), 85 (7%), 55 (7%).

Workup

  1. additionpoured onto water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f680eef43a0642539c879b79785ea9e0
Source dataset
uspto-grants-2004_02
Patent number
US06689290B2

Reaction notes

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