Water → HCID 21514922, compound

HRID 1576266Notes

Reaction equation

HRID 1576266 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[O:18][CH3:19])[C:8]([CH2:24][C:25](O)=[O:26])([CH2:20][C:21](O)=[O:22])[C:7]=2[CH:6]=[CH:5][CH:4]=1.B#B.O>O1CCCC1>[OH:26][CH2:25][CH2:24][C:8]1([CH2:20][CH2:21][OH:22])[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[C:14]=2[CH2:15][C:16]2[C:7]1=[CH:6][CH:5]=[CH:4][C:3]=2[O:2][CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6328200DiboronHCID 21514916HCID 21514916, compound

Product 1

HCID 21514922HCID 21514922, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 4,5-dimethoxy-10-oxo-9,10-dihydroanthracene-9,9-diacetic acid (9.9 g.) in dry tetrahydrofuran (300 ml.) is added with stirring, in an atmosphere of nitrogen, diborane in tetrahydrofuran (1M, 100 ml.). The reaction mixture is refluxed for 72 hours, cooled, and water (100 ml.) is added. The tetrahydrofuran is evaporated and the remaining suspension is filtered, the residue is washed successively with aqueous sodium bicarbonate, water, a little isopropanol, and petroleum ether (b.p. 60°-80°C.) to give 9,9-di-(2-hydroxyethyl)-4,5-dimethoxy-9,10-dihydroanthracene, m.p. 193°-196°C.

Workup

  1. temperatureThe reaction mixture is refluxed for 72 hours
  2. temperaturecooled
  3. customThe tetrahydrofuran is evaporated
  4. filtrationthe remaining suspension is filtered
  5. washthe residue is washed successively with aqueous sodium bicarbonate, water

Sources & evidence

ORD record
ord-9a8b89bff2ff4c2a9000b11959e8f178
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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