4-(1,1-Dimethyl-2-propynyloxy)anisole → 6-Methoxy-2,2-dimethyl-2H-1-benzopyran

HRID 2425354Notes

Reaction equation

HRID 2425354 reaction equation
[CH3:1][C:2]([CH3:14])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[C:3]#[CH:4]>ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:2]([CH3:14])([CH3:1])[CH:3]=[CH:4][C:7]=2[CH:8]=1

Participants

3

Reactant 1

HCID 118302224-(1,1-Dimethyl-2-propynyloxy)anisole

Product 1

HCID 117454246-Methoxy-2,2-dimethyl-2H-1-benzopyranYield 61%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 4-(1,1-dimethyl-2-propynyloxy)anisole in 1,2-dichlorobenzene (50 mL) was stirred at 190° C. for 2 hours. Upon the completion of the reaction, the solvent was distilled off under a reduced pressure. The residue was purified by column chromatography (hexane/chloroform=3/1) and the aimed product was obtained as red oily substance (2-step, yield: 61%).

Workup

  1. customUpon the completion of the reaction
  2. distillationthe solvent was distilled off under a reduced pressure
  3. customThe residue was purified by column chromatography (hexane/chloroform=3/1)

Sources & evidence

ORD record
ord-0b9a3817ad3f4c0ab2521405dab92837
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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