Acetyl chloride → HCID 59129379, compound

HRID 1847696Notes

Reaction equation

HRID 1847696 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].C[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([C:20]([O:22][CH3:23])=[O:21])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>C(=S)=S>[CH3:23][O:22][C:20]([C:17]1([C:14]2[CH:15]=[CH:16][C:11]([OH:10])=[C:12]([C:5](=[O:7])[CH3:6])[CH:13]=2)[CH2:19][CH2:18]1)=[O:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13707544Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylate

Product 1

HCID 59129379HCID 59129379, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred suspension of AlCl3 (58 g, 440 mmol) in CS2 (500 mL) was added acetyl chloride (7.4 g, 95 mmol) at room temperature. After stirring for 5 min, methyl 1-(4-methoxyphenyl)cyclopropanecarboxylate (15 g, 73 mmol) was added. The reaction mixture was heated at reflux for 2 h before ice water was added carefully to the mixture at room temperature. The resulting mixture was extracted with EtOAc (150 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 1-(3-acetyl-4-hydroxy-phenyl)-cyclopropanecarboxylic methyl ester (15 g, 81%), which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 12.28 (s, 1H), 7.67 (d, J=2.0 Hz, 1H), 7.47 (dd, J=2.0, 8.4 Hz, 1H), 6.94 (d, J=8.4 Hz, 1H), 3.64 (s, 3H), 2.64 (s, 3H), 1.65-1.62 (m, 2H), 1.18-1.16 (m, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwas added carefully to the mixture at room temperature
  3. extractionThe resulting mixture was extracted with EtOAc (150 mL×3)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-981e865ccf40439bb62ddb3577308412
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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