Hydrochloric Acid → 2-Methyl-2-phenyl-6,7-dichloroindan-1,5-diol

HRID 597034Notes

Reaction equation

HRID 597034 reaction equation
[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([OH:11])[CH:8]=2)[C:3]1=[O:14].[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>O1CCCC1.C1C=CC=CC=1>[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([OH:11])[CH:8]=2)[CH:3]1[OH:14]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 936906,7-Dichloro-5-hydroxy-2-methyl-2-phenylindan-1-oneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 214494762-Methyl-2-phenyl-6,7-dichloroindan-1,5-diol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2-methyl-2-phenyl-5-hydroxy-6,7-dichloro-1-indanone (14.3 g., 0.047 mole) in tetrahydrofuran (150 ml.) under nitrogen is added dropwise over a 10 minute period 70% sodium bis(2-methoxyethoxy) aluminum hydride in benzene (17 ml.) in tetrahydrofuran (50 ml.) while maintaining the reaction temperature at 10°-15° C. The reaction mixture is stirred at 25° C. for 26 hours, cooled to 10° C, slowly treated with 10% hydrochloric acid until frothing ceases, then with 20% hydrochloric acid until acidic. The tetrahydrofuran is decanted from a pasty residue, evaporated to dryness and the residue taken up in benzene (300 ml.). The insoluble, homogeneous product which separates at this stage is primarily 2-methyl-2-phenyl-6,7-dichloroindane-1,5-diol (α-isomer), 800 mg., m.p. 177°-181° C. and is used without further purification. The benzene solution is dried over magnesium sulfate and evaporated to dryness to give 8.57 g. of a mixture of isomers. Three crystallizations from benzene gives 3.0 g. of 2-methyl-2-phenyl-6,7-dichloroindan-1,5-diol (β-isomer), m.p. 163°-165° C. and is used in Example 18 below without further purification.

Workup

  1. temperaturewhile maintaining the reaction temperature at 10°-15° C
  2. temperaturecooled to 10° C
  3. customThe tetrahydrofuran is decanted from a pasty residue
  4. customevaporated to dryness
  5. custom, m.p. 177°-181° C. and is used without further purification
  6. dry with materialThe benzene solution is dried over magnesium sulfate
  7. customevaporated to dryness
  8. customto give 8.57 g
  9. additionof a mixture of isomers
  10. customThree crystallizations from benzene
  11. customgives 3.0 g
  12. customof 2-methyl-2-phenyl-6,7-dichloroindan-1,5-diol (β-isomer), m.p. 163°-165° C. and is used in Example 18 below without further purification

Sources & evidence

ORD record
ord-24db3b35e19b4eef813d37a99e668383
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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