Methanesulfonyl chloride → HCID 14570276, compound

HRID 1414547Notes

Reaction equation

HRID 1414547 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1([CH2:23][CH2:24][OH:25])[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2>N1C=CC=CC=1>[CH3:1][S:2]([O:25][CH2:24][CH2:23][C:9]1([CH2:8][CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[O:16][C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 145702752,2'-(9H-Xanthene-9,9-diyl)di(ethan-1-ol)

Product 1

HCID 14570276HCID 14570276, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 9,9-bis(2'-vinyloxyethyl)xanthene (57 g.) (prepared as in Example 2), water (400 ml.) and concentrated hydrochloric acid (15 ml.) is heated on the steambath with vigorous stirring for 5 hours. The cooled mixture is extracted three times with ether and the combined extracts are dried over MgSO4 and evaporated to dryness. The solid residue is recrystallised from chloroform-light petroleum (b.p. 60°-80° C.) to give 9,9-bis(2'-hydroxyethyl)xanthene, m.p. 144°-145° C. Methanesulphonyl chloride (588 mg.) is added dropwise over 5 minutes at 5° C. to a solution of 9,9-bis(2'-hydroxyethyl)xanthene (0.54 g.) in dry pyridine (5 ml.) with stirring. The mixture is allowed to stand at room temperature for 20 hours and is then poured into a mixture of 3N hydrocholoric acid (20 ml.) and ice (10 g.), and the resulting mixture is extracted with ethyl acetate. The ethyl acetate extract is washed with 3N hydrochloric acid and water, dried over MgSO4, and evaporated to dryness. The solid residue is recrystallised from acetone-light petroleum (b.p. 60°-80° C.) to give 9,9-bis(2'-methanesulphonyloxyethyl)-xanthene, m.p. 121°-122° C.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washis washed with 3N hydrochloric acid and water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe solid residue is recrystallised from acetone-light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-aba5891ce3ad4618b1846965e62d2f5d
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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