Hydrochloric Acid → HCID 82165586, compound

HRID 2419373Notes

Reaction equation

HRID 2419373 reaction equation
[S:1]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:13][CH2:14][C:15]([C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:4]=1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 123375Acetic acid, (phenylthio)-, methyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 82165586HCID 82165586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl thiophenoxyacetate (60g.) in methylene chloride (100ml.) was added over 20 minutes to a stirred suspension of chloroacetyl chloride (45.2g.) and aluminium chloride (134g.) in methylene chloride (400ml.) at room temperature. The resulting solution was stirred at room temperature overnight and poured onto a mixture of ice (2kg.) and concentrated hydrochloric acid (50ml.). This mixture was then stirred at room temperature for 1 hour. The methylene chloride phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was recrystallised from methanol to give methyl 4-(chloroacetyl)-thiophenoxyacetate (60.1g.), m.p. 61°-63° C.

Workup

  1. stirringThis mixture was then stirred at room temperature for 1 hour
  2. customThe methylene chloride phase was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-2b23168e15db4278a733228a020bb0dd
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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