Potassium Iodide → HCID 22709072, compound

HRID 1739498Notes

Reaction equation

HRID 1739498 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.Cl[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 748286-Chloro-1-hexanol

Product 1

HCID 22709072HCID 22709072, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5 g of 6-bromo-2-naphthol, 50 ml of dimethyl sulphoxide, 3.3 ml of 6-chlorohexanol, 7.1 g of potassium iodide and 7.1 g of potassium carbonate (ground and activated at 80° C. in a high vacuum) was heated to 65° C. for 16 hrs. Then, the mixture was cooled, partitioned between ethyl acetate and water, and the organic phase was washed several times with water, dried over magnesium sulphate, filtered and evaporated. Chromatography of the residue on 200 g of silica gel with toluene/ethyl acetate (3:1) and subsequent crystallization form toluene/hexane (8:1) gave 5.2 g of 6-bromo-2-(6-hydroxyhexyloxy)naphthalene as a colorless solid.

Workup

  1. customactivated at 80° C. in a high vacuum
  2. temperatureThen, the mixture was cooled
  3. custompartitioned between ethyl acetate and water
  4. washthe organic phase was washed several times with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b97c58fce2bd4042868634ede3ad0b48
Source dataset
uspto-grants-1999_10
Patent number
US05965761

Reaction notes

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