Hydrofluoric Acid → 4,4-Dimethylchroman

HRID 1382911Notes

Reaction equation

HRID 1382911 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:3].F>C(OCC)C>[CH3:3][C:2]1([CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 12441681[(3-Methylbut-3-en-1-yl)oxy]benzene

Product 1

HCID 3167634,4-DimethylchromanYield 92.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 19.2 g 2-methyl-4-phenoxy-1-butene and 50 ml of anhydrous hydrogen fluoride was stored at room temperature for 3 days. The mixture was then diluted with 500 ml of diethyl ether and the resulting mixture was washed with saturated sodium bicarbonate solution (2×500 ml). It was then dried (MgSO4) and concentrated in vacuo to give 17.7 g of the title compound as an oil. Yield 92%.

Workup

  1. washthe resulting mixture was washed with saturated sodium bicarbonate solution (2×500 ml)
  2. dry with materialIt was then dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aba54213446b462481e628146fb0d3e7
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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