Hydrochloric Acid → 3,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyran

HRID 637628Notes

Reaction equation

HRID 637628 reaction equation
Br[CH:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=1[OH:15].[H-].[Na+].Cl>CS(C)=O>[CH3:16][CH:2]1[CH2:3][CH2:4][C:5]2[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=2[O:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 135602952-(3-Bromobutyl)-3-methyl-6-nitrophenol

Product 1

HCID 135602963,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40.5 g of 1C was added in portions over 20 minutes to a stirred mixture of 3.4 g of sodium hydride in 300 ml of DMSO at room temperature, and the resulting mixture was stirred for 18 hours at room temperature. The mixture was poured into ice water, made slightly acidic with concentrated hydrochloric acid and filtered. The solid was dried to give 3,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyran (1D) as a yellow solid, m.p.: 83°-85° C.

Workup

  1. filtrationfiltered
  2. customThe solid was dried

Sources & evidence

ORD record
ord-a75eae1efd71446e90da5a071a985273
Source dataset
uspto-grants-1985_12
Patent number
US04558040

Reaction notes

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