Water → HCID 13187522, compound

HRID 462464Notes

Reaction equation

HRID 462464 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:22][CH2:23][O:24][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)(=O)=O.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:22][CH2:23][O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 13187521HCID 13187521, compound

Product 1

HCID 13187522HCID 13187522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 24 g (0.12 mol) of 4-benzyloxyphenol in 100 cc of DMF is added dropwise to a 50% suspension of 6.2 g (0.132 mol) of NaH in 50 cc of DMF. When the evolution of gas has ended, a solution of 36 g (0.127 mol) of 2-cyclopentyloxyethyl tosylate in 100 cc of DMF is then added. The mixture is stirred for half an hour. It is then heated for 2 hours at 55°-60° C. with stirring. The reaction mixture is poured into iced water. Extraction is carried out with diethyl ether. The ether phase is washed with dilute sodium hydroxide solution and then with water, dried and evaporated to dryness.

Workup

  1. temperatureIt is then heated for 2 hours at 55°-60° C.
  2. stirringwith stirring
  3. extractionExtraction
  4. washThe ether phase is washed with dilute sodium hydroxide solution
  5. dry with materialwith water, dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1c126ba7edd94729ab868398eb363528
Source dataset
uspto-grants-1985_05
Patent number
US04515814

Reaction notes

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