Dimethylformamide → HCID 10830577, compound

HRID 2371663Notes

Reaction equation

HRID 2371663 reaction equation
CN(C)C=O.[C:6]([O:15][CH2:16][CH3:17])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O.C(OCC)(=O)C>[CH2:16]([O:15][C:6](=[O:14])[C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[O:9][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])[CH3:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8365Ethyl SalicylateHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 10830577HCID 10830577, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

200 ml of N,N-dimethylformamide was added to 18.3 g of ethyl salicylate, and 34.5 g of potassium carbonate and 24.9 g of lauryl bromide were added thereto dropwise over about 30 min with stirring on a steam bath. After the addition the reaction mixture was heated for 2 hours with stirring, then after cooling it was transferred into a separately funnel, and 300 ml of ethyl acetate and 1l of water were added for extraction. The ethyl acetate solution was washed with dilute hydrochloric acid and then with an aqueous sodium hydrogencarbonate solution and was concentrated, to obtain an oil of 2-dodecyloxybenzoic acid ethyl ester. The oil was dissolved in 300 ml of ethanol, and a solution of 12 g of sodium hydroxide in 50 ml of water was added dropwise thereto over about 10 min at room temperature with stirring. After the addition stirring was continued for 1 hour further and 30 ml of concentrated hydrochloric acid diluted with 300 ml of water was added dropwise. The deposited crystals were filtered, washed with water, and dried to obtain 29.1 g of 2-dodecyloxybenzoic acid.

Workup

  1. additionwere added
  2. additionAfter the addition the reaction mixture
  3. temperaturewas heated for 2 hours
  4. stirringwith stirring
  5. temperatureafter cooling it
  6. additionwere added for extraction
  7. washThe ethyl acetate solution was washed with dilute hydrochloric acid
  8. concentrationwith an aqueous sodium hydrogencarbonate solution and was concentrated

Sources & evidence

ORD record
ord-01f15fbcd6124b81bb85dbf2771819dc
Source dataset
uspto-grants-1992_03
Patent number
US05094938

Reaction notes

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