1-Butanol → 3,5-Dihydroxyadamantane-1-carboxylic acid

HRID 1699157

Reaction equation

HRID 1699157 reaction equation
[OH:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([OH:11])([CH2:10][C:4]([C:13]([OH:15])=[O:14])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:16](O)[CH2:17][CH2:18][CH3:19].S(=O)(=O)(O)O.[Cl-].[Na+].[OH-].[Na+]>>[OH:11][C:8]12[CH2:7][CH:6]3[CH2:12][C:2]([OH:1])([CH2:3][C:4]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])([CH2:5]3)[CH2:10]1)[CH2:9]2.[OH:11][C:8]12[CH2:7][CH:6]3[CH2:12][C:2]([OH:1])([CH2:3][C:4]([C:13]([OH:15])=[O:14])([CH2:5]3)[CH2:10]1)[CH2:9]2

Participants

7

Reactant 5

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 120106473,5-Dihydroxyadamantane-1-carboxylic acid

Product 2

HCID 120106473,5-Dihydroxyadamantane-1-carboxylic acidHCID 23435153n-Butyl 3,5-dihydroxy-adamantanecarboxylate

Conditions

Temperature
100 °C

Procedure

A mixture of 0.14 mol of the obtained 3,5-dihydroxy-1-adamantanecarboxylic acid, 1.4 mol of n-butanol and 3.5 mmol of sulfuric acid was stirred at 100° C. for 8 hours. To the reaction mixture were added a saturated sodium chloride aqueous solution and a 5% sodium hydroxide aqueous solution (NaOH: 3.5 mmol), and the resultant mixture was subjected to separation. The organic layer was concentrated, and the concentrated residue was subjected to recrystallization from toluene to give n-butyl 3,5-dihydroxy-1-adamantanecarboxylate in yield of 86% at a conversion rate from 3,5-dihydroxy-1-adamantanecarboxylic acid of 99%.

Workup

  1. concentrationThe organic layer was concentrated
  2. customthe concentrated residue was subjected to recrystallization from toluene

Sources & evidence

ORD record
ord-eb09486dd79645b1b39e70efa4f16fc8
Source dataset
uspto-grants-2002_02
Patent number
US06344590B1

Linked notes

Loading…