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

HRID 2286889Notes

Reaction equation

HRID 2286889 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 3 N hydrochloric acid (20 ml.) and ice (10 g.), and the resulting mixture is extracted with ethyl acetate. The ethyl acetate extract is washed with 3 N 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-722a994bd2cf4d4a87ac6360f864899e
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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