[3-(Hydroxymethyl)-1-adamantyl]methanol → HCID 15483193, compound

HRID 910427Notes

Reaction equation

HRID 910427 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][C:16]([CH2:24][OH:25])([CH2:17]3)[CH2:15]1)[CH2:21]2>C(Cl)Cl.C1COCC1.C(OCC)C>[C:14]12([CH:13]=[O:12])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][C:16]([CH:24]=[O:25])([CH2:17]3)[CH2:15]1)[CH2:21]2

Participants

6

Reactant 2

HCID 703011[3-(Hydroxymethyl)-1-adamantyl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 15483193HCID 15483193, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of pyridinium chlorochromate (PCC, 0.850 g, 4.0 mmol) in CH2Cl2 (˜10 mL) was added a suspension of 1,3-bis(hydroxymethyl)adamantane (0.196 g, 1.0 mmol) in anhydrous THF (˜5 mL). The reaction mixture was stirred at room temperature for 2.5 hours, whereupon it was diluted with anhydrous diethyl ether (˜50 mL) and filtered through a plug of florisil. The filtrate was evaporated in vacuo to afford dicarbaldehyde (0.183 g, 95%). According to GC analysis (DB 210, 150° C.), product had a purity of over 95%. Since dialdehyde is unstable and decomposes on silica gel, the sample was used in the next step without further purification.

Workup

  1. additionwas added
  2. filtrationfiltered through a plug of florisil
  3. customThe filtrate was evaporated in vacuo
  4. customto afford dicarbaldehyde (0.183 g, 95%)
  5. customAccording to GC analysis (DB 210, 150° C.), product
  6. customthe sample was used in the next step without further purification

Sources & evidence

ORD record
ord-d55428e7848345ccb8a88c1b499ebfe5
Source dataset
uspto-grants-2011_09
Patent number
US08022097B2

Reaction notes

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