Methanol → Dimethyl 1,3-adamantanedicarboxylate

HRID 1937244Notes

Reaction equation

[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([C:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][C:17]([C:25](O)=[O:26])([CH2:18]3)[CH2:16]1)[CH2:22]2)([OH:14])=[O:13].[CH3:28][OH:29]>>[CH3:28][O:29][C:25]([C:17]12[CH2:18][CH:19]3[CH2:20][CH:21]([CH2:22][C:15]([C:12]([O:14][CH3:1])=[O:13])([CH2:24]3)[CH2:16]1)[CH2:23]2)=[O:26]

Participants

Reactant 3

HCID 887Methanol

HCID 6101p-Toluenesulfonic acid

HCID 643391,3-Adamantanedicarboxylic acid

Product 1

HCID 365223Dimethyl 1,3-adamantanedicarboxylate

Procedure

In the presence of an acid catalyst (p-toluenesulfonic acid), 1,3-dicarboxyadamantane obtained in Example 2 was allowed to react with an excess amount of methanol to give 1,3-dimethoxycarbonyladamantane.

Sources & evidence

ORD record: ord-5ac0f9e6d78240e28f1f8bcb20c0db95
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06392104B1

Reaction notes

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