Dichloromethane → HCID 54165251, compound

HRID 1701713Notes

Reaction equation

HRID 1701713 reaction equation
[C:1]1([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24].C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[C:19]1([C:23]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:2][CH:3]=2)=[O:24])[S:18][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 789282-Thiophenecarbonyl chlorideHCID 1482829Ethyl [(naphthalen-1-yl)oxy]acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54165251HCID 54165251, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

483 g ethyl 1-naphthyloxyacetate and 308 g thiophene-2-carboxylic acid chloride was dissolved in 3.570 l. methylene chloride. While the mixture is being maintained at about -10° C., 291 g aluminium chloride are introduced slowly; after 2 hours at -10° C., the mixture is brought back to 25° C. and the stirring maintained for 12 hours. The mixture is then poured into 2 Kg iced water, the organic phase decanted off, washed with dilute aqueous sodium hydroxide solution then water and the solvent evaporated. 562 g of the ester are thus obtained. After recrystallisation from isopropyl ether, it melts at 79° C.

Workup

  1. customis brought back to 25° C.
  2. temperaturethe stirring maintained for 12 hours
  3. customthe organic phase decanted off
  4. washwashed with dilute aqueous sodium hydroxide solution
  5. customwater and the solvent evaporated

Sources & evidence

ORD record
ord-04719df485754765bc17cb9507ab7dea
Source dataset
uspto-grants-1980_03
Patent number
US04195093

Reaction notes

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