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

HRID 2209577Notes

Reaction equation

HRID 2209577 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-a462e78a8c5941c2bb4bb1ab41df553e
Source dataset
uspto-grants-1995_10
Patent number
US05455246

Reaction notes

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