Isobutyryl chloride → Methyl 2-[5-isobutyryl-1-naphthyl]propionate

HRID 223713Notes

Reaction equation

HRID 223713 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>C(Cl)Cl>[C:21]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][CH:6]=[C:5]2[CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17])(=[O:25])[CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12535017Methyl 2-(naphthalen-1-YL)propanoate

Product 1

HCID 12535026Methyl 2-[5-isobutyryl-1-naphthyl]propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under vigorous magnetic stirring, CH2Cl2 (125 cc) followed by AlCl3 (60 g) are added to a 500 cc three-necked flask provided with a cooling device with CaCl2 trap, a dropping funnel and a thermometer (said three-necked flask being immersed in a water-bath maintained at room temperature). Methyl 2-(1-naphthyl)-propionate (32.1 g) and isobutyryl chloride (18 cc) dissolved in CH2Cl2 (100 cc) are added thereto dropwise. The addition takes 2.5 hours. On completion of the addition, the ingredients are maintained in contact, with continued stirring. Hydrolysis is effected by pouring the reaction mixture over ice-water. The material is extracted with ether. The organic phase is washed over Na2SO4 ; the ether and CH2Cl2 are distilled off and the residual oil is distilled, to give the product named in the title.

Workup

  1. additionare added to a 500 cc three-necked flask
  2. customprovided with a cooling device with CaCl2 trap, a dropping funnel
  3. additionare added
  4. additionThe addition
  5. additionOn completion of the addition
  6. temperaturethe ingredients are maintained in contact, with continued stirring
  7. customHydrolysis
  8. extractionThe material is extracted with ether
  9. washThe organic phase is washed over Na2SO4
  10. distillationthe ether and CH2Cl2 are distilled off
  11. distillationthe residual oil is distilled
  12. customto give the product

Sources & evidence

ORD record
ord-577302f5a0e94de588290020fb93c2d1
Source dataset
uspto-grants-1982_10
Patent number
US04356188

Reaction notes

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