Dimethylformamide → 2-ethoxy-6-pentadecyl-benzoyl Chloride

HRID 2055890Notes

Reaction equation

HRID 2055890 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:5]=1[C:6](O)=[O:7])[CH3:2].S(Cl)([Cl:30])=O.CN(C)C=O>CCCCCC>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:5]=1[C:6]([Cl:30])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 684514982-Ethoxy-6-pentadecylbenzoic Acid

Product 1

HCID 102500672-ethoxy-6-pentadecyl-benzoyl Chloride

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 2-Ethoxy-6-pentadecylbenzoic Acid (6.5 g, 16 mmol) in hexane (60 mL) were added thionyl chloride (2.5 g, 21 mmol) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux for 1 h After the reaction was complete, the solvent was evaporated under reduced pressure to yield the desired 2-Ethoxy-6-pentadecylbenzoyl Chloride, which was redissolved in dichloromethane (50 mL) and used for the condensation with anilides.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h After the reaction
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0f1cce07bede4d6cb274bc0d211044c4
Source dataset
uspto-grants-2008_02
Patent number
US07332629B2

Reaction notes

Loading…