Hydrochloric Acid → 2,2'-(9H-Xanthene-9,9-diyl)di(ethan-1-ol)

HRID 1414546Notes

Reaction equation

HRID 1414546 reaction equation
C([O:3][CH2:4][CH2:5][C:6]1([CH2:20][CH2:21][O:22]C=C)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=C.Cl>O>[OH:22][CH2:21][CH2:20][C:6]1([CH2:5][CH2:4][OH:3])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[O:13][C:14]2[C:19]1=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 234605239,9-Bis[2-(ethenyloxy)ethyl]-9H-xanthene

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. temperatureis heated on the steambath
  2. extractionThe cooled mixture is extracted three times with ether
  3. dry with materialthe combined extracts are dried over MgSO4
  4. customevaporated to dryness
  5. customThe solid residue is recrystallised from chloroform-light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-d33d0aed6a8c42c5ae5217c207f632cf
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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