Cesium carbonate → HCID 21280526, compound

HRID 1285486Notes

Reaction equation

HRID 1285486 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][Cl:9].[OH:10][C:11]1[CH:12]=[C:13]([CH:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Cs+]>CC(C)=O>[ClH:9].[OH:23][CH:17]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 24601Cesium iodideHCID 117900843-(1-Hydroxyhexyl)phenol

Product 1

HCID 21280526HCID 21280526, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 3.3 g of picolyl chloride hydrochloride (Aldrich 16,270-1), 1-(3-hydroxyphenyl)-1-hexanol (3.9 g.), cesium carbonate (16.3 g.), cesium iodide (trace) and acetone was refluxed for 40 hours. The reaction was filtered through a pad of celite and silica gel and the solvent removed in vacuo. The remaining oil was dissolved in ethyl ether, filtered through celite and silica gel and treated with ethereal hydrochloric acid. The resulting white precipitate was filtered, washed (ethyl ether) and dried giving 4.2 g (66% yield) of solid, m.p. 164°-165° C.

Workup

  1. temperaturewas refluxed for 40 hours
  2. filtrationThe reaction was filtered through a pad of celite and silica gel
  3. customthe solvent removed in vacuo
  4. dissolutionThe remaining oil was dissolved in ethyl ether
  5. filtrationfiltered through celite and silica gel
  6. additiontreated with ethereal hydrochloric acid
  7. filtrationThe resulting white precipitate was filtered
  8. washwashed (ethyl ether)
  9. customdried

Sources & evidence

ORD record
ord-95537e2691b747de8a63efeadcc1ae14
Source dataset
uspto-grants-1986_01
Patent number
US04567184

Reaction notes

Loading…