Hydrochloric Acid → Methyl 4-hydroxyadamantane-1-carboxylate

HRID 1424567Notes

Reaction equation

HRID 1424567 reaction equation
[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([OH:14])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.Cl.O1CCOC[CH2:17]1>CO>[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:17])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 45525374-hydroxyadamantane-1-carboxylic Acid

Product 1

HCID 3741502Methyl 4-hydroxyadamantane-1-carboxylateYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-hydroxyadamantane-1-carboxylic acid (4.47 g, 22.8 mmol) in MeOH (75 mL) was added 4 M HCl in dioxane (25 mL, 100 mmol). The mixture was stirred at rt for 2 d and concentrated. The residue was purified by chromatography on a 40-g silica cartridge eluted with a 0-80% EtOAc in hexanes gradient to afford methyl 4-hydroxyadamantane-1-carboxylate (4.04 g, 84%) as a clear, colorless oil.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on a 40-g silica cartridge
  3. washeluted with a 0-80% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-28e953b600f34dfdb6eb5a0db25b32a6
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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