Benzoyl chloride → 3-Benzoyloxy-4-chlorotoluene

HRID 1685651Notes

Reaction equation

HRID 1685651 reaction equation
[C:1]([O:9][C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[CH:14][C:15]=1F)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18]C1C=CC(C)=CC=1O.C(Cl)(=O)C1C=CC=CC=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:9][C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[CH:14][C:15]=1[Cl:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 120082-Chloro-5-methylphenolHCID 167492203-Benzoyloxy-4-fluorotoluene

Product 1

HCID 167492223-Benzoyloxy-4-chlorotolueneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by adapting the method for 3-benzoyloxy-4-fluorotoluene using 4-chloro-3-hydroxytoluene (3.92 g, 27.5 mmol), benzoyl chloride (3.51 g, 25 mmol) and NEt3 (5 mL) in CH2Cl2 (100 mL) to give 3-benzoyloxy-4-chlorotoluene as a white solid (5.82 g, 94%), which was used without further purification. δH (400 MHz, CDCl3) 2.38 (s, 3H,), 7.05 (d, J=8.2, 1H), 7.11 (s, 1H), 7.36 (d, J=8.2, 1H), 7.51-7.56 (m, 2H), 7.64-7.70 (m, 1H), 8.22-8.28 (m, 2H); δC (100 MHz, CDCl3) 21.41, 123.97, 124.58, 128.07, 128.85, 129.15, 130.07, 130.55, 134.01, 138.38, 146.98, 164.51.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-70ee28e52caa4f83b0b7d47f0bc65a9a
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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