Water → HCID 13086534, compound

HRID 365631Notes

Reaction equation

HRID 365631 reaction equation
[CH3:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([OH:12])([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:13](OC(=O)C)(=[O:15])[CH3:14].S(=O)(=O)(O)O.O.C(=O)(O)[O-].[Na+]>CCCCCCC.C1CCCCC1.CCOCC>[C:13]([O:12][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][C:2]([CH3:1])([CH2:11]3)[CH2:3]1)[CH2:10]2)(=[O:15])[CH3:14]

Participants

9

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 40715573-METHYL-1-ADAMANTANOL

Product 1

HCID 13086534HCID 13086534, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolventHCID 8900HeptaneSolvent

Procedure

121 mg (0.728 mmoles) of 3-methyl-1-adamantanol are dissolved in 0.2 mL n-heptane and 0.2 mL cyclohexane. A mixture of 0.2 mL (2.25 mmoles) of acetic anhydride and 2 microliters (0.036 mmoles) of concentrated sulfuric acid is added, and the mixture is stirred at ambient temperature for 20.5 hours. The solution is dissolved in 10L of ether and extracted with 10 mL of water. The aqueous layer is extracted with 10 mL ether. The ether layers are combined, extracted with 2×mL of water followed by 40 mL of aqueous sodium bicarbonate (10 g/liter), dried over magnesium sulfate, and stripped of solvent in vacuo. The product is a colorless oil with Rf 0.55 (silica: eluant hexane 75%, ethyl acetate 25%).

Workup

  1. additionis added
  2. extractionextracted with 10 mL of water
  3. extractionThe aqueous layer is extracted with 10 mL ether
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-59afb346da8d49eeab55639c82d39cfe
Source dataset
uspto-grants-2000_10
Patent number
US06127415

Reaction notes

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