Hydrochloric Acid → HCID 19782199, compound

HRID 258022Notes

Reaction equation

HRID 258022 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([C:11]([OH:13])=[O:12])[CH2:5]2.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:18][C:19]([CH3:24])=[CH:20][C:21](Cl)=[O:22].Cl>[N+](C1C=CC=CC=1)([O-])=O.C(Cl)Cl.C(=S)=S>[CH3:18][C:19]1([CH3:24])[CH2:20][C:21](=[O:22])[C:10]2[CH:9]=[C:8]3[CH2:7][CH:6]([C:11]([OH:13])=[O:12])[CH2:5][C:4]3=[CH:3][C:2]=2[O:1]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1023943-Methyl-2-butenoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 19782180HCID 19782180, compound

Product 1

HCID 19782199HCID 19782199, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6348Carbon DisulfideSolventHCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
90 °C

Procedure

9.8 g (5.5 mmol) of 5-hydroxy-indan-2-carboxylic acid are dissolved in 20 ml of nitrobenzene and 20 ml of carbon disulphide and 16.12 g (121 mmol) of aluminum trichloride are added in portions. 7.8 g (66 mmol) of dimethylacryloyl chloride in 20 ml of nitrobenzene are then added dropwise and the mixture is heated to 90° C. for 3 h. After cooling, 40 ml of concentrated hydrochloric acid and 40 g of ice are added and the mixture is shaken twice with 100 ml of CH2Cl2 each time. The combined CH2Cl2 phases are evaporated, the nitrobenzene is distilled off in a water jet vacuum and the residue is taken up in 100 ml of 10% strength NaOH solution. The NaOH phase is shaken twice with 100 ml of CH2Cl2 each time, then acidified using concentrated HCl solution with ice cooling and extracted 3 times using 100 ml of CH2Cl2 each time. After drying over Na2SO4, the solution is evaporated and the residue is flash chromatographed on silica gel (eluent: CH2Cl2 /acetone 10:1)

Workup

  1. temperatureAfter cooling
  2. customThe combined CH2Cl2 phases are evaporated
  3. distillationthe nitrobenzene is distilled off in a water jet vacuum
  4. extractionextracted 3 times
  5. dry with materialAfter drying over Na2SO4
  6. customthe solution is evaporated
  7. customchromatographed on silica gel (eluent: CH2Cl2 /acetone 10:1)

Sources & evidence

ORD record
ord-f6173fd9bb7b4ce8a971bc06b070d0c4
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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