1-Chloro-4-(chloromethyl)benzene → HCID 12361851, compound

HRID 1077338Notes

Reaction equation

HRID 1077338 reaction equation
C(OC1CC2C3[C:15](=CC=CC=3)[NH:14][C:13]=2CC1)(=O)C1C=CC=CC=1.[H-].[Na+].ClC1C=CC(CCl)=CC=1.C(O[CH:43]1[CH2:55][C:54]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=3)[C:46]=2[CH2:45][CH2:44]1)(=O)C1C=CC=CC=1>O.CN(C)C=O>[Cl:63][C:60]1[CH:61]=[CH:62][C:57]([CH2:56][N:47]2[C:46]3[CH2:45][CH2:44][CH:43]([N:14]([CH3:15])[CH3:13])[CH2:55][C:54]=3[C:53]3[C:48]2=[CH:49][CH:50]=[CH:51][CH:52]=3)=[CH:58][CH:59]=1

Participants

7

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 12891847HCID 12891847, compoundHCID 23470342HCID 23470342, compound

Product 1

HCID 12361851HCID 12361851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 29.1 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole and 4.3 g. of sodium hydride (56% in mineral oil) in 200 ml. of dimethylformamide was heated on a steam bath and 16.1 g. of p-chlorobenzyl chloride in 30 ml. of dimethylformamide was added dropwise. The reaction mixture was heated 2 hours, cooled, and diluted with water. The resulting oil was washed with water and crystallized from isopropyl alcohol to give 12.7 g. of 3-benzoyloxy-9-(p-chlorobenzyl)-1,2,3,4-tetrahydrocarbazole, m.p. 150°-152°C.

Workup

  1. additionA mixture of 29.1 g
  2. temperatureThe reaction mixture was heated 2 hours
  3. temperaturecooled
  4. washThe resulting oil was washed with water
  5. customcrystallized from isopropyl alcohol
  6. customto give 12.7 g

Sources & evidence

ORD record
ord-e8af2ac7a60e4092a78ac17785a8cdd1
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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