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

HRID 1439306
Notes
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Reaction equation

HRID 1439306 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
10 °C

Procedure

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 block. After filtration and dilution with water, the 4-hydroxy-3-hydroxymethyl-2-pentyl 4-(n-hexadecylamino)benzoate is obtained as a white solid.

Workup

  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 block
  6. filtrationAfter filtration and dilution with water

Sources & evidence

ORD record
ord-90709a3b73d541599a5ed1b0b5d4c205
Source dataset
uspto-grants-1977_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04058550

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes