Acetyl chloride → HCID 18401031, compound

HRID 1019363Notes

Reaction equation

HRID 1019363 reaction equation
[Br-].[Br-].[Br-].[Al+3].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1>ClCCl>[C:5]([C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][C:13]=1[CH2:17][C:18]([OH:20])=[O:19])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 15719(3-Methoxyphenyl)acetic acidHCID 166749Bromhydrol

Product 1

HCID 18401031HCID 18401031, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of aluminum tribromide (57.6 g, 216 mmol) in dichloromethane (90 mL) at 0° C. was slowly added acetyl chloride (11.5 mL, 162 mmol). To the reaction mixture was added (3-methoxy-phenyl)-acetic acid (17.9 g, 108 mmol) in dichloromethane (20.0 mL). The reaction mixture was stirred for one hour and then poured over ice (100 mL). The organic layer was separated and 1N aqueous sodium hydroxide was added (100 mL). The biphasic mixture was stirred vigorously for 90 minutes and the layers were separated. The organic layer was discarded and concentrated hydrochloric acid was added to the aqueous layer until the pH reached 1. A solid precipitated and was filtered and air-dried to afford (2-acetyl-5-methoxy-phenyl)-acetic acid (16.8 g, 75%). M.p. 153-155° C. 1H NMR (300 MHz, CDCl3) δ2.68 (s, 3), 3.91 (s, 3), 3.92 (s, 2), 6.92-6.95 (m, 2), 7.88 (d, 1, J=9.5). 13C NMR (100 MHz, CDCl3) δ28.33, 41.43, 55.46, 112.54, 118.26, 129.17, 133.08, 136.94, 162.65, 174.80, 200.96. IR 3435, 1704, 1663, 1609, 1568, 1258 cm−1. Analysis calculated for C11H12O4: C, 63.45; H, 5.81. Found: C, 63.35; H, 5.46.

Workup

  1. customat 0° C.
  2. customThe organic layer was separated
  3. addition1N aqueous sodium hydroxide was added (100 mL)
  4. stirringThe biphasic mixture was stirred vigorously for 90 minutes
  5. customthe layers were separated
  6. additionconcentrated hydrochloric acid was added to the aqueous layer until the pH
  7. customA solid precipitated
  8. filtrationwas filtered
  9. customair-dried

Sources & evidence

ORD record
ord-305e709ff5a34cc5a901bf75c70d8c09
Source dataset
uspto-grants-2002_11
Patent number
US06486325B1

Reaction notes

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