Hydrofluoric Acid → 6-Chloro-7-methoxy-2-methylchroman-4-one

HRID 1722046Notes

Reaction equation

HRID 1722046 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH3:12])[CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[O:15][CH3:16].F>>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5](=[CH:4][C:3]=1[O:15][CH3:16])[O:6][CH:7]([CH3:12])[CH2:8][C:9]2=[O:11]

Participants

4

Reactant 3

HCID 14917Hydrofluoric AcidHCID 157499673-(4-Chloro-3-methoxyphenoxy)butyric acidHCID 178435160HCID 178435160, compound

Product 1

HCID 138500436-Chloro-7-methoxy-2-methylchroman-4-one

Procedure

In a polyethylene bottle were combined 3.3 g (13 mmol) 3-(4-chloro-3-methoxyphenoxy)butyric acid and 30 ml liquid hydrogen fluoride. The reaction mixture was allowed to stand at 23° C. for 72 hours, then poured over ice and extracted with 2×100 ml diethyl ether. The ether was washed with 2×100 ml water, 100 ml saturated sodium bicarbonate and brine, dried over magnesium sulfate and concentrated in vacuo to give the product as a yellow solid, 2.7 g (93%).

Workup

  1. additionpoured over ice
  2. extractionextracted with 2×100 ml diethyl ether
  3. washThe ether was washed with 2×100 ml water, 100 ml saturated sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0b5d337c2de4548b151326918a5babf
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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