1-Butanol → n-Butyl 3-hydroxy-1-adamantanecarboxylate

HRID 1699153Notes

Reaction equation

HRID 1699153 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([OH:14])=[O:13])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:15](O)[CH2:16][CH2:17][CH3:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 27365183-Hydroxyadamantane-1-carboxylic acid

Product 1

HCID 12010642n-Butyl 3-hydroxy-1-adamantanecarboxylateYield 94.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 900 ml of toluene were added 300 mmol of the obtained 3-hydroxy-1-adamantanecarboxylic acid, 450 mmol of n-butanol, and 15 mmol of sulfuric acid, and the resultant mixture was stirred under reflux of toluene for 5 hours. The reaction mixture was concentrated and then subjected to column chromatography on a silica gel to give n-butyl 3-hydroxy-1-adamantanecarboxylate (yield: 94.1%). The conversion rate from 3-hydroxy-1-adamantanecarboxylic acid was 99%.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-36629ce6b6314eb0a99ce8ab0e6d78b8
Source dataset
uspto-grants-2002_02
Patent number
US06344590B1

Reaction notes

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