4-Nitrobenzoyl chloride → HCID 68444400, compound

HRID 889513Notes

Reaction equation

HRID 889513 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][CH:14]([CH:18]=[CH:19][CH3:20])[CH2:15][CH2:16][OH:17]>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:17][CH2:16][CH2:15][CH:14]([CH3:13])[CH:18]=[CH:19][CH3:20])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 53797562HCID 53797562, compound

Product 1

HCID 68444400HCID 68444400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of freshly crystallized 4-nitrobenzoyl chloride (10.1 g, 54.5 mmol) in CH2Cl2 (ml 20) was added dropwise to a solution of 3-methyl-hex-4-en-1-ol (5.4 g, 47.5 mmol) and TEA (8.6 ml, 61.8 mmol) in CH2Cl2 (ml 50) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 1 h and poured in ice/water (100 g). The CH2Cl2 was separated and the water phase was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was distilled at 171-173° C. 4 mmHg to give the title compound as yellow oil.

Workup

  1. customThe CH2Cl2 was separated
  2. extractionthe water phase was extracted twice with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. distillationThe crude product was distilled at 171-173° C

Sources & evidence

ORD record
ord-0482ece71ab744bd9d18d2ceac1a9278
Source dataset
uspto-grants-2012_08
Patent number
US08252825B2

Reaction notes

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