Oxalyl chloride → Benzeneacetyl chloride, 2,4,6-tris(1-methylethyl)-

HRID 2393264Notes

Reaction equation

HRID 2393264 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[CH2:16][C:17]([OH:19])=O)([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:23])=O>CN(C)C=O>[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[CH2:16][C:17]([Cl:23])=[O:19])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 105156412,4,6-Triisopropylphenylacetic acid

Product 1

HCID 10516914Benzeneacetyl chloride, 2,4,6-tris(1-methylethyl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2,4,6-triisopropylphenylacetic acid (6.03 g, 0.023 mol), oxalyl chloride (20 mL), and dimethylformamide (3 drops) was stirred vigorously at room temperature and then allowed to stand overnight at room temperature. The reaction mixture was then concentrated to give the product as an off-white solid 6.5 g, 100%. This was used directly in the next step.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-a47f54cb53de4a549647d04151498dd6
Source dataset
uspto-grants-1998_09
Patent number
US05807846

Reaction notes

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