Sodium Hydroxide → HCID 22158838, compound

HRID 1607633Notes

Reaction equation

HRID 1607633 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:16])[CH2:9][C:10]([CH3:15])([CH3:14])[O:11]2)=[CH:6][CH:5]=1.Br[CH2:18][O:19][CH3:20]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[CH3:18][O:19][CH2:20][O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:16])[CH2:9][C:10]([CH3:14])([CH3:15])[O:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 83093Bromomethyl methyl etherHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 22158838HCID 22158838, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 20 ml of 10% sodium hydroxide solution, 50 ml of dichloro methane, 0.5 g (2 millimoles) of triethyl benzyl ammonium chloride and 0.9 g (10 millimoles) of 7-hydroxy-2,2-dimethyl-4-chromanone is intensively stirred at 20° C. for 30 minutes. To the mixture 3.1 g (2 ml, 25 millimoles) of bromomethyl-methyl-ether are added. The reaction mixture is stirred for a further 30 minutes, the organic phase is separated, washed twice with 50 ml. of water each, dried and the solvent is removed. The residue is crystallized from 70% ethanol. Thus 2.1 g of the desired compound are obtained, yield 90%. Mp.: 77°-79° C.

Workup

  1. stirringThe reaction mixture is stirred for a further 30 minutes
  2. customthe organic phase is separated
  3. washwashed twice with 50 ml
  4. dry with materialof water each, dried
  5. customthe solvent is removed
  6. customThe residue is crystallized from 70% ethanol

Sources & evidence

ORD record
ord-6dba374e99f04aedba815f853c222418
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

Loading…