Water → HCID 22041763, compound

HRID 1790290Notes

Reaction equation

HRID 1790290 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][CH:4]=1.[C:15](Cl)(=[O:18])[CH2:16][CH3:17].[Cl-].[Al+3].[Cl-].[Cl-].O>ClC(Cl)C>[CH3:14][O:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:15](=[O:18])[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 62324Propionyl chlorideHCID 823371,4-DimethoxynaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22041763HCID 22041763, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a cold solution (ice bath) of 1,4-dimethoxy-naphthalene (5 g, 26.6 mmol) in dichloroethane (100 mL) was added propionyl chloride (2.7 g, 29.3 mmol) followed by aluminum chloride (3.9 g, 29.3 mmol). After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 4 hr. Water (200 mL) was added and the organic material was extracted with dichloromethane (200 mL). The organic extracts were dried (MgSO4) and concentrated to give a residue which was purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9) to give an oil (1.4 g): 1H NMR (DMSO-d6) δ 1.16 (t, 3H, CH3), 3.13 (q, 2H, CH2), 3.87 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 7.02 (s, 1H, Ar—H), 7.67 (m, 2H, Ar—H), 8.10 (d, 2H, Ar—H); MS 245 (M+1).

Workup

  1. additionAfter the addition
  2. extractionthe organic material was extracted with dichloromethane (200 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane: 1/9)

Sources & evidence

ORD record
ord-e7432b3077a04dd99c20e2dcc8995da1
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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