Thionyl Chloride → (9S, 10S)-2-Chloro-9,10-dihydro-9,10-methano-9-anthracenecarbonyl chloride

HRID 258284Notes

Reaction equation

HRID 258284 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@H:12]3[CH2:16][C@:5]([C:17]([OH:19])=O)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@H:12]3[CH2:16][C@:5]([C:17]([Cl:22])=[O:19])([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67637562(9S,10S)-2-chloro-9,10-dihydro-9,10-methano-9-anthracenecarboxylic acid

Product 1

HCID 57139020(9S, 10S)-2-Chloro-9,10-dihydro-9,10-methano-9-anthracenecarbonyl chlorideYield 100.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of (9S, 10S)-2-chloro-9,10-dihydro-9,10-methano-9-anthracenecarboxylic acid (1.0 g, 3.62 mmol), prepared as described in Example 109a, in toluene (10 mL) was added thionyl chloride (0.29 mL, 3.98 mmol). After refluxing for 1.5 h, the mixture was concentrated to give the title compound as a light yellow solid (1.05 g, quant.); MS(CI): 289 (M+H).

Workup

  1. customprepared
  2. temperatureAfter refluxing for 1.5 h
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-0d03c655645d47d68d5a5565eeab27c2
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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