Hydrochloric Acid → 2,2-Dimethyl-4-(naphthalen-1-yl)-2H-1-benzopyran-7-ol

HRID 838907

Reaction equation

HRID 838907 reaction equation
[CH3:1][Li].[OH:3][C:4]1C=C2[C:7]([C:8]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)=[CH:9]C(=O)O2)=[CH:6][CH:5]=1.Cl.[CH3:26][CH2:27][O:28][CH2:29][CH3:30]>>[CH3:26][C:27]1([CH3:1])[CH:9]=[C:8]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:7]2[C:29](=[CH:30][C:4]([OH:3])=[CH:5][CH:6]=2)[O:28]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 233307447-Hydroxy-4-(1-naphthyl)coumarinHCID 178418348HCID 178418348, compound

Product 1

HCID 233307472,2-Dimethyl-4-(naphthalen-1-yl)-2H-1-benzopyran-7-olYield 95%

Procedure

To a stirred solution of methyl-lithium in ether (60ml, 2M solution) at room temperature was added over 0.5 hours 7-hydroxy-4-(1-naphthyl)coumarin (7.5g, 0.025 moles). The reaction mixture was refluxed for 2 hours, allowed to cool and decomposed by the addition of dilute hydrochloric acid. The organic layer was separated, the aqueous layer extracted with ether (2×) and the combined organic extracts washed with water and dried. Removal of solvent gave the required title chromene as an orange oil (7.22g, 95%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperatureto cool
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ether (2×)
  5. washthe combined organic extracts washed with water
  6. customdried
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-c481da294f0a4b9da60f3b5b369bed63
Source dataset
uspto-grants-1978_06
Patent number
US04093631

Linked notes

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