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1-Butanol → 5-Hydroxy-1,3-adamantanedicarboxylic acid

HRID 1699156
Notes
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Reaction equation

HRID 1699156 reaction equation
[OH:1][C:2]12[CH2:11][C:6]3([C:12]([OH:14])=[O:13])[CH2:7][CH:8]([CH2:10][C:4]([C:15]([OH:17])=[O:16])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:18](O)[CH2:19][CH2:20][CH3:21].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]12[CH2:3][C:4]3([C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])[CH2:10][CH:8]([CH2:7][C:6]([C:12]([O:14][CH2:9][CH2:2][CH2:3][CH3:4])=[O:13])([CH2:5]3)[CH2:11]1)[CH2:9]2.[OH:1][C:2]12[CH2:3][C:4]3([C:15]([OH:17])=[O:16])[CH2:10][CH:8]([CH2:7][C:6]([C:12]([OH:14])=[O:13])([CH2:5]3)[CH2:11]1)[CH2:9]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 120106445-Hydroxy-1,3-adamantanedicarboxylic acid

Product 2

HCID 120106445-Hydroxy-1,3-adamantanedicarboxylic acidHCID 12010645Di-n-butyl 5-hydroxy-1,3-adamantanedicarboxylate

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To 900 ml of toulene were added 300 mmol of the obtained 5-hydroxy-1,3-adamantanedicarboxylic acid, 900 mmol of n-butanol and 30 mmol of sulfuric acid, and the resultant mixture was stirred under reflux of toluene for 5 hours. The reaction mixture was concentrated and subjected to column chromatogrpahy on a silica gel to give di-n-butyl 5-hydroxy-1,3-adamantanedicarboxylate in yield of 85.5% at a conversion rate from 5-hydroxy-1,3-adamantanedicarboxylic acid of 95%.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-48627ff0b9a94b349901d5b7b7f2f2ec
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344590B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes