Acetyl chloride → HCID 53767267, compound

HRID 327953Notes

Reaction equation

HRID 327953 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20].[C:23](Cl)(=[O:25])[CH3:24].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:23](=[O:25])[CH3:24])[CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 53736567HCID 53736567, compound

Product 1

HCID 53767267HCID 53767267, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.3 g (13.96 mmol) of 2-[[5-(acetoxy)pentyl]oxy]benzenepropanoic acid methyl ester and 2.18 g (27.8 mmol) of freshly distilled acetyl chloride in 250 mL of dry dichloromethane was stirred with ice-bath cooling while 7.5 g (56.7 mmol) of anhydrous aluminum chloride was added in one portion. The resulting mixture was stirred at 0°-5° C. for 2 hr before being treated with ice. Work-up with dichloromethane in the usual manner gave an oil which was chromatographed on 100 g of silica gel. Elution with 1:1 hexane-ether afforded 4.22 g (86.4%) of 2-[[5-(acetoxy)pentyl]oxy]-5-acetylbenzenepropanoic acid methyl ester as an almost colorless oil.

Workup

  1. additionwas added in one portion
  2. additionbefore being treated with ice
  3. customgave an oil which
  4. customwas chromatographed on 100 g of silica gel
  5. washElution with 1:1 hexane-ether

Sources & evidence

ORD record
ord-116b2952f2444393a9dca82fb3bea010
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

Loading…