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Benzyl Chloride → 4-Hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate

HRID 615064
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HRID 615064 반응식
[OH:1][CH:2]([CH:4]([CH2:8][OH:9])[CH:5]([OH:7])[CH3:6])[CH3:3].[H-].[Na+].[H][H].C(Cl)C1C=CC=CC=1.Cl.[CH2:23]([NH:39][C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(COC)OC.CN(C)C1C=CN=CC=1.O.C(Cl)(Cl)Cl>[CH2:23]([NH:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]([O:1][CH:2]([CH:4]([CH2:8][OH:9])[CH:5]([OH:7])[CH3:6])[CH3:3])=[O:45])=[CH:47][CH:48]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 612343-(Hydroxymethyl)pentane-2,4-diolHCID 132553224-Hexadecylaminobenzoyl chloride hydrochlorideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 213269404-Hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate

시약·촉매·용매

4
HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6212Chloroform용매HCID 80711,2-Dimethoxyethane용매

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온도
10 °C

실험 절차

A 13.4 g. of 2,4-dihydroxy-3-hydroxymethylpentane solution in dimethoxyethane is added to 2.4 g. of sodium hydride (washed free of mineral oil). After hydrogen evolution ceased, 12.65 g. of benzyl chloride is added and the mixture refluxed for 4 hours. After cooling to 10° C., 24.4 g. of 4-dimethylaminopyridine and 41.6 g. of 4-(n-hexadecylamino)benzoyl chloride hydrochloride are added. Chloroform and water are added after 16 hours and the chloroform extract is dried and evaporated to dryness. The residue is dissolved in acetic acid and hydrogenated at 30 psi hydrogen pressure over palladium black. After filtration and dilution with water, the 4-hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate is obtained as a white solid.

후처리

  1. temperaturethe mixture refluxed for 4 hours
  2. extractionthe chloroform extract
  3. customis dried
  4. customevaporated to dryness
  5. dissolutionThe residue is dissolved in acetic acid and hydrogenated at 30 psi hydrogen pressure over palladium black
  6. filtrationAfter filtration and dilution with water

출처 및 근거

ORD 기록
ord-6d963bd4a3ce435a80c0f0f5b9540ab1
출처 데이터셋
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04146546

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