Benzene → 8-Methoxy-2,2-dimethyl-7-(2-methylpropoxy)-2H-1-benzopyran

HRID 986841Notes

Reaction equation

HRID 986841 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[C:8]([O:17][CH3:18])[C:7]=1[OH:19])[CH:2]=[C:3]([CH3:5])[CH3:4].C1C=CC=CC=1>CCCCCC>[CH2:13]([O:12][C:9]1[C:8]([O:17][CH3:18])=[C:7]2[C:6]([CH:1]=[CH:2][C:3]([CH3:4])([CH3:5])[O:19]2)=[CH:11][CH:10]=1)[CH:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 241BenzeneHCID 20156627HCID 20156627, compound

Product 1

HCID 1797868-Methoxy-2,2-dimethyl-7-(2-methylpropoxy)-2H-1-benzopyranYield 80%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 5.8 g (22 millimoles) of 2-prenyl-5-isobutoxy-6-methoxy-phenol, a molar equivalent amount of methyl-trialkyl (C8 -C10)-ammonium dichromane and 100 ml of benzene is refluxed for 10 hours. The reaction mixture is diluted with hexane, washed with 20% sodium thiosulfate, the organic phase is dried, evaporated and the residue is purified by column chromatography (see Example 3). Thus 4.6 g of the desired compound are obtained in the form of a colorless oil, yield 80%.

Workup

  1. washwashed with 20% sodium thiosulfate
  2. customthe organic phase is dried
  3. customevaporated
  4. customthe residue is purified by column chromatography (see Example 3)

Sources & evidence

ORD record
ord-5bfd5c9bf39a4219af33a63aacc57a42
Source dataset
uspto-grants-1987_12
Patent number
US04716238

Reaction notes

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