4-Chlorobutyryl chloride → Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

HRID 887695Notes

Reaction equation

HRID 887695 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:17])[C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9].[Cl:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23]>>[CH3:5][O:6][C:7](=[O:17])[C:8]([C:10]1[CH:11]=[CH:12][C:13]([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][Cl:18])=[CH:14][CH:15]=1)([CH3:9])[CH3:16]

Participants

4

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 143498Methyl 2-methyl-2-phenylpropanoate2×HCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 10062338Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetateYield 110.9%

Conditions

Temperature
-10 °C

Procedure

MDC (600 ml) and aluminium chloride (347 gms) were charged to a reactor and chilled to −10° C. Methyl-2-methyl-2 phenyl-propanoate (Intermediate 4) (500 gms) was dissolved in MDC (650 ml) and added slowly through a dropper at −10 to 0° C. to obtain mixture A. MDC (600 ml) and aluminium chloride (520 gms) were charged to a different reactor, and chilled to −10° C. 4-chloro butyryl chloride (550 gms) was dissolved in MDC (650 ml) and added slowly through a dropper at −10 to 0° C. to obtain mixture B. Both mixtures A and B were stirred for 45 minutes at −10 to 0° C. separately. Mixture A was added to mixture B slowly at −10 to 0° C. and the reaction monitored by GC for completion (24 hours). The mass was quenched slowly in conc. HCl (1 ltr) at 10-20° C. and stirred for 30 minutes. The MDC layer was separated and the aqueous layer extracted with MDC (500 ml). The combined MDC layer was dried over sodium sulfate and concentrated under vacuum to obtain 880 gms of the title compound as an oil.

Workup

  1. additionadded slowly through a dropper at −10 to 0° C.
  2. customto obtain mixture A
  3. temperaturechilled to −10° C
  4. additionadded slowly through a dropper at −10 to 0° C.
  5. customto obtain mixture B
  6. additionMixture A was added to mixture B slowly at −10 to 0° C.
  7. custommonitored by GC for completion (24 hours)
  8. customThe mass was quenched slowly in conc. HCl (1 ltr) at 10-20° C.
  9. stirringstirred for 30 minutes
  10. customThe MDC layer was separated
  11. extractionthe aqueous layer extracted with MDC (500 ml)
  12. dry with materialThe combined MDC layer was dried over sodium sulfate
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f2589af29f504801830fd3fa47604bc0
Source dataset
uspto-grants-2012_08
Patent number
US08247434B2

Reaction notes

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