Water → 7-(3-Chloropropoxy)-2-(hydroxymethyl)-chromen-4-one

HRID 635224Notes

Reaction equation

HRID 635224 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[CH:7]=[C:8]([CH2:12][OH:13])[O:9]2)=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.CN(C)C=O.C(OCC)C>[Cl:19][CH2:18][CH2:17][CH2:16][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[CH:7]=[C:8]([CH2:12][OH:13])[O:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 105119297-Hydroxy-2-(hydroxymethyl)-chromen-4-one

Product 1

HCID 105398897-(3-Chloropropoxy)-2-(hydroxymethyl)-chromen-4-oneYield 50.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 g (31 mmoles) of the compound obtained in Example 4, 6 mL (61 mmoles) of 1-bromo-3-chloropropane, 4.3 g (31 mmoles) of anhydrous potassium carbonate in 100 mL of acetone and 25 mL of N,N-dimethylformamide was heated at reflux for 16 hours. The reaction mixture was poured onto 100 mL of water and extracted with 100 mL of ethyl acetate. The organic extracts were washed with two portions of 100 mL of water, dried over sodium sulphate and evaporated at vaccum. The residue obtained was suspended in 25 mL of ethyl ether, filtered and dried at vaccum to give 4.2 g of 7-(3-chloropropoxy)-2-(hydroxymethyl)-chromen-4-one in 50% yield, mp 110-112° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. extractionextracted with 100 mL of ethyl acetate
  4. washThe organic extracts were washed with two portions of 100 mL of water
  5. dry with materialdried over sodium sulphate
  6. customevaporated at vaccum
  7. customThe residue obtained
  8. filtrationfiltered
  9. customdried at vaccum

Sources & evidence

ORD record
ord-8cada6448cd843e0a0804d1dc57a3877
Source dataset
uspto-grants-2001_02
Patent number
US06187793B1

Reaction notes

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