Benzoyl chloride → HCID 19604550, compound

HRID 1604737Notes

Reaction equation

HRID 1604737 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[OH:21])[CH:16]=[O:17])([O-:12])=[O:11].C(N(CC)CC)C>C(Cl)Cl>[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:16]=[O:17])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 19604550HCID 19604550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzoyl chloride (2.50 mL, 20.0 mmol) in methylene chloride (100 mL) cooled at 0° C. was added 3-nitro-4-hydroxybenzaldehyde (3.00 g, 19.0 mmol) and triethylamine (2.80 mL, 20.0 mmol). After 1 hour the mixture was washed with water and concentrated to an oil, in vacuo. The product was crystallized from ethyl acetate-hexane giving 1.70 g (33.0%); mp110.5-112° C. 1H NMR (CDCl3): 10.05 (s,1H,CHO), 8.59 (s,1H) 8.20 (m,3H), 7.62 (2,1H), 7.38 (m,3H). MS (DCl) 272 (MH+). C14H9NO5.

Workup

  1. washAfter 1 hour the mixture was washed with water
  2. concentrationconcentrated to an oil, in vacuo
  3. customThe product was crystallized from ethyl acetate-hexane giving 1.70 g (33.0%)

Sources & evidence

ORD record
ord-152eea2576324764ab12a7e4bb894c49
Source dataset
uspto-grants-1999_11
Patent number
US05994563

Reaction notes

Loading…