Thionyl Chloride → 3-(4-t-Butylphenyl)propionyl chloride

HRID 1017146Notes

Reaction equation

HRID 1017146 reaction equation
C[Si](C)(C)C1C=C(Br)C=C([Si](C)(C)C)C=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=O)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].S(Cl)([Cl:33])=O>CN(C)C=O.C(Cl)Cl.C(C1C=CC(CCC(O)=O)=CC=1)(C)(C)C>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([Cl:33])=[O:30])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 49621733-(4-Tert-butylphenyl)propanoic acidHCID 12884904(5-Bromo-1,3-phenylene)bis(trimethylsilane)

Product 1

HCID 184028883-(4-t-Butylphenyl)propionyl chlorideYield 76.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 49621733-(4-Tert-butylphenyl)propanoic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A 2 L 3 neck round bottom flask fit with a condenser, thermometer, nitrogen inlet, and overhead stirrer was charged with 3-(4-t-butylphenyl)propionic acid (118.7 g, 0.576 mol),thionyl chloride (210 mL, 2.88 mol), dimethylformamide (3 drops), and methylene chloride solvent. The reaction was refluxed for 3 hours and additional 3-(4-t-butylphenyl)propionic acid (8.17 g, 0.040 mol) was added to the reactor and refluxed for an additional hour. After allowing to stand overnight, the reaction was stripped of volatiles to yield the crude 3-(4-t-butylphenyl)propionyl chloride (99.0 g). 1HNMR (CDCl3, 500 MHz) δ7.33 (d, JAB=8 Hz, 2H); 7.12 (d, JAB=8 Hz, 2H); 3.20 (t, J=7.5 Hz, 2H); 2.98 (t, J=7.5, 2H); 1.31 (s, 9H).

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. temperaturerefluxed for an additional hour

Sources & evidence

ORD record
ord-e680c120a49a438ba181fd2af4e3854c
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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