Acetyl chloride → HCID 767785, compound

HRID 2273041Notes

Reaction equation

HRID 2273041 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([CH:11]2[CH2:16][CH2:15][CH:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl>[C:17]([CH:14]1[CH2:15][CH2:16][CH:11]([C:5]2[CH:10]=[CH:9][C:8]([C:20](=[O:22])[CH3:21])=[CH:7][CH:6]=2)[CH2:12][CH2:13]1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 1288374921060-31-1

Product 1

HCID 767785HCID 767785, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of AlCl3 (5.9 g, 54 mmol) in DCM (200 mL) at 0° C. was added 1-(4-phenylcyclohexyl)ethanone (9 g in DCM), and acetyl chloride (10.4 mL, 146 mmol) dropwise over 30 min. The mixture was stirred to rt for 15 min. and heated at 45° C. for 4 h. After being cooled to rt, the mixture was poured it into ice-HCl (1N). The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were combined, concentrated and purified on column (hexane:ethyl acetate, 8:2) to give 1-(4-(4-acetylcyclohexyl)phenyl)ethanone (A2) as a mixture of two isomers (5 g, 46% yield).

Workup

  1. temperatureheated at 45° C. for 4 h
  2. temperatureAfter being cooled to rt
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  5. concentrationconcentrated
  6. custompurified on column (hexane:ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-5aacef1781a341468d9033786605ddd6
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

Loading…