Stearoyl chloride → HCID 13393454, compound

HRID 615485Notes

Reaction equation

HRID 615485 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:13](Cl)(=[O:31])[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][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>O1CCCC1>[C:13]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH2:11][CH3:12])=[O:9])(=[O:31])[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][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8365Ethyl SalicylateHCID 8471Triethylamine

Product 1

HCID 13393454HCID 13393454, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (+5° C.) solution of ethyl salicylate (0.136 moles) and stearoyl chloride (0.136 moles) in tetrahydrofuran (200 ml) was added triethylamine (0.136 moles) dropwise over 25 min. After refluxing for 20 hours, the solution was cooled to room temperature. Most of the tetrahydrofuran was removed with a N2 stream during the cooling process. The residue was poured into ice/water (1500 ml), stirred for 1 hour, and a white solid removed by filtration. Washing the solid with water, followed by air drying gave 56 g of the title product, m.p. 50.5°-53.5° C.

Workup

  1. temperatureAfter refluxing for 20 hours
  2. customMost of the tetrahydrofuran was removed with a N2 stream during the cooling process
  3. additionThe residue was poured into ice/water (1500 ml)
  4. customa white solid removed by filtration
  5. washWashing the solid with water
  6. customdrying

Sources & evidence

ORD record
ord-649c5bc61da84d229806a4f95a9babce
Source dataset
uspto-grants-1985_02
Patent number
US04499295

Reaction notes

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