Dichloromethane → HCID 21518641, compound

HRID 1283638Notes

Reaction equation

HRID 1283638 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([CH3:26])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19].C(Cl)Cl>O>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[C:9]=1[C:18](=[O:19])[C:17]1[CH:21]=[C:22]([CH3:26])[C:23]([O:24][CH3:25])=[C:15]([CH3:14])[CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 779512-ButylbenzofuranHCID 214353833,5-Dimethyl-4-methoxybenzoyl chloride

Product 1

HCID 21518641HCID 21518641, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (ice bath) mixture of 9.4 g. (0.054 mol.) of 2-n-butylbenzofuran and 11.5 g. (0.058 mol.) of 3,5-dimethyl-4-methoxybenzoic acid chloride in 100 ml. of methylene chloride was added dropwise 28.7 g. (0.11 mol.) of stannic chloride. The reaction mixture was allowed to warm to ambient temperature, then stirred for 2 hours. Water was slowly added to the mixture and it was stirred an additional 30 minutes. The layers were separated and the organic phase was washed with water until the washings were neutral, dried (MgSO4) and concentrated to give 2-n-butyl-3-(3',5'-dimethyl-4'-methoxybenzoyl)benzofuran.

Workup

  1. temperatureTo a cooled
  2. addition(ice bath) mixture of 9.4 g
  3. stirringwas stirred an additional 30 minutes
  4. customThe layers were separated
  5. washthe organic phase was washed with water until the washings
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6448438676854acbbbd17feaeeedbf02
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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