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

HRID 224932Notes

Reaction equation

HRID 224932 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 (60 ml, 2 M solution) at room temperature was added over 0.5 hours 7-hydroxy-4-(1-naphthyl)coumarin (7.5 g, 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 (2x) and the combined organic extracts washed with water and dried. Removal of solvent gave the required title chromene as an orange oil (7.22 g, 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 (2x)
  5. washthe combined organic extracts washed with water
  6. customdried
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-e43e89f5fb5d4ae686b25fb8dd71106f
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Reaction notes

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