3-Hydroxyadamantane-1-carboxylic acid → 3-(Hydroxymethyl)adamantan-1-ol

HRID 1978112Notes

Reaction equation

HRID 1978112 reaction equation
[OH-].[Li+].[Al+3].[OH-].[OH-].[OH-].[C:7]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([OH:20])([CH2:13]3)[CH2:11]1)[CH2:17]2)(O)=[O:8]>O1CCCC1>[OH:8][CH2:7][C:10]12[CH2:17][CH:16]3[CH2:15][CH:14]([CH2:13][C:12]([OH:20])([CH2:18]3)[CH2:11]1)[CH2:19]2

Participants

4

Reactant 2

HCID 27365183-Hydroxyadamantane-1-carboxylic acid2×HCID 16206110Aluminate (Al(OH)41-), lithium, (T-4)-

Product 1

HCID 120704753-(Hydroxymethyl)adamantan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 mmol of aluminiumlitium hydroxide was suspended in 15 ml of tetrahydrofuran (THF) in a nitrogen atmosphere. To the solution was slowly added 10 mmol of the 1-carboxy-3-adamantanol obtained in Preparation Example 5 while the temperature of the solution was maintained at less than 10° C. or below by ice water bath. After the temperature of the mixture was raised to room temperatures, the mixture was refluxed for 16 hours. And, as the result, the 1-carboxy-3-adamantanol was converted into a 1-hydroxymethyl-3-adamantanol (yield: 95%) with a conversion of 99%.

Workup

  1. customobtained in Preparation Example 5 while the temperature of the solution
  2. temperaturewas maintained at less than 10° C. or below by ice water bath
  3. temperatureAfter the temperature of the mixture was raised to room temperatures
  4. temperaturethe mixture was refluxed for 16 hours

Sources & evidence

ORD record
ord-898c22bb2ea045139386614c904381fa
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

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