Methanol → Dimethyl 1,3-adamantanedicarboxylate

HRID 992162Notes

Reaction equation

HRID 992162 reaction equation
S(Cl)(Cl)=O.[CH2:5](N(CC)CC)C.[CH3:12][OH:13].[C:14]([C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][C:19]([C:27](O)=[O:28])([CH2:20]3)[CH2:18]1)[CH2:24]2)([OH:16])=[O:15]>CN(C=O)C>[CH3:12][O:13][C:27]([C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][C:17]([C:14]([O:16][CH3:5])=[O:15])([CH2:26]3)[CH2:18]1)[CH2:25]2)=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 643391,3-Adamantanedicarboxylic acid

Product 1

HCID 365223Dimethyl 1,3-adamantanedicarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3-dicarboxyadamantane obtained by the method of Example 64 was dissolved in 10 ml of DMF. To the mixture, 30 mmole of thionyl chloride was added dropwise over 30 minutes and the mixture was heated to begin to reflux around the conclusion of addition. After refluxing for 2 hours, the mixture was cooled. To the mixture, 40 mmole of triethylamine was added followed by 22 mmole of methanol over 30 minutes while retaining the temperature of the mixture at 10° C. or less, and then stirred for more 2 hours. As a result, the conversion of 1, 3-dicarboxyadamantane was 99%, and 1,3-bis(methoxycarbonyl)adamantane (yield 95%) was formed.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux around the conclusion of addition
  3. temperatureAfter refluxing for 2 hours
  4. temperaturethe mixture was cooled
  5. customat 10° C. or less

Sources & evidence

ORD record
ord-1f35c0cca70f468797b4d178f76c3b51
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Reaction notes

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