Thionyl Chloride → 4-(4-Benzyloxy-3-chloromethylphenoxy)-5-methyl-7-nitroindane

HRID 1766650Notes

Reaction equation

HRID 1766650 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]3[C:17]=2[CH2:18][CH2:19][CH2:20]3)=[CH:11][C:10]=1[CH2:29]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:33])=O>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]3[C:17]=2[CH2:18][CH2:19][CH2:20]3)=[CH:11][C:10]=1[CH2:29][Cl:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23031098[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanol

Product 1

HCID 230311674-(4-Benzyloxy-3-chloromethylphenoxy)-5-methyl-7-nitroindane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

[2-benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]methanol (2.48 g) was dissolved in diethyl ether. After adding dropwise thionyl chloride (5 mL) under ice-cooling with stirring, the mixture was stirred at room temperature for 6 hours. The reaction mixture was evaporated under reduced pressure to dryness. After adding water (10 mL), the residue was extracted with diethyl ether. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (2.04 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 6 hours
  3. customThe reaction mixture was evaporated under reduced pressure to dryness
  4. additionAfter adding water (10 mL)
  5. extractionthe residue was extracted with diethyl ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0580df68c11b4842a5f286b946988595
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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