Hydrochloric Acid → 4,5'-Dimethylangelicin

HRID 848155Notes

Reaction equation

HRID 848155 reaction equation
[Na].C([O:5][C:6]1[C:15]([CH2:16][CH:17](Br)[CH2:18]Br)=[C:14]2[C:9]([C:10]([CH3:22])=[CH:11][C:12](=[O:21])[O:13]2)=[CH:8][CH:7]=1)(=O)C.Cl>C(O)C>[CH3:22][C:10]1[C:9]2[CH:8]=[CH:7][C:6]3[O:5][C:17]([CH3:18])=[CH:16][C:15]=3[C:14]=2[O:13][C:12](=[O:21])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 12900451HCID 12900451, compound

Product 1

HCID 613224,5'-DimethylangelicinYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium (29.8 g, 1.296 mol) in dry, absolute ethanol (1400 ml.) was added to 7-acetoxy-4-methyl-8-(2', 3'-dibromopropyl)coumarin (108.1 g, 0.259 mol). The mixture was allowed to reflux for one hour and 45 minutes with magnetic stirring. The cooled mixture was poured into a mixture of ice (2800 g) and 3.5% HCl (2800 ml.) and stirred. A yellow precipitate was collected by filtration, washed first with three portions (600 ml.) of 5% NaOH, second with one portion (600 ml.) of 3.5% HCl, third with three portions (600 ml.) of water, and then dried in vacuo to obtain crude 4,8-dimethylisopsoralen (48.6 g, 87.6% yield, mp. 160°-174° C.). Recrystallization from 95% ethanol (1500 ml.) gave the pure product (33.7 g, 68% recovery, 61% yield) mp. 176°-178° C. (lit.2 182°-183° C.).

Workup

  1. temperatureto reflux for one hour and 45 minutes with magnetic stirring
  2. filtrationA yellow precipitate was collected by filtration
  3. washwashed first with three portions (600 ml.) of 5% NaOH, second with one portion (600 ml.) of 3.5% HCl, third with three portions (600 ml.) of water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-62f3b4ac62cb4278aa5e2423a5cf313c
Source dataset
uspto-grants-1981_10
Patent number
US04294847

Reaction notes

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