Potassium Iodide → 6-Hydroxy-7-sec. butoxy-2,2-dimethyl-4-chromanone

HRID 1607641Notes

Reaction equation

HRID 1607641 reaction equation
[CH3:1][C:2]([CH2:4][CH3:5])=O.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(Br)(CC)C.[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[OH:30])[O:26][C:25]([CH3:32])([CH3:31])[CH2:24][C:23]2=[O:33]>>[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[O:30][CH:2]([CH2:4][CH3:5])[CH3:1])[O:26][C:25]([CH3:31])([CH3:32])[CH2:24][C:23]2=[O:33]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 65542-BromobutaneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 126377192,2-Dimethyl-6,7-dihydroxy-4-chromanone

Product 1

HCID 143349736-Hydroxy-7-sec. butoxy-2,2-dimethyl-4-chromanoneYield 86%

Procedure

In 100 ml of methyl-ethyl-ketone 4.2 g (20 millimoles) of 6,7-dihydroxy-2,2-dimethyl-4-chromanone are dissolved and to the solution thus obtained 4.1 g (30 millimoles) of potassium carbonate, 0.5 g of potassium iodide and 3.3 g (2.6 millimoles, 24 millimoles) of sec. butyl bromide are added under stirring. The reaction mixture is heated to boiling for 12 hours. The reaction mixture is worked up according to Example 17. Thus 4.5 g of the desired compound are obtained, yield 86%, mp.: 114°-116° C.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated

Sources & evidence

ORD record
ord-8a4ab18e7e3c4afe94f4a6bf9f095d62
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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