Water → HCID 22639372, compound

HRID 2415003Notes

Reaction equation

HRID 2415003 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[C:10]12(O)[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2.[OH2:21]>[OH-].[K+].C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:9])[CH:7]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)[OH:21])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 641521-AdamantanolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22639372HCID 22639372, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14797Potassium HydroxideSolvent

Procedure

29.26 g (150 mmol) of bromoacetic acid-tert-butyl ester is added at 0° C. to 15.22 g (100 mmol) of 1-adamantanol in 300 ml of 50% aqueous potassium hydroxide solution, 200 ml of toluene, and it is vigorously and thoroughly stirred for 2 hours. It is poured onto 1500 ml of water and extracted 2 times with 300 ml of diethyl ether. The combined organic phases are dried on magnesium sulfate and evaporated to the dry state in a vacuum. The residue is chromatographed on silica gel (mobile solvent: n-hexane/diethyl ether 20:1).

Workup

  1. extractionextracted 2 times with 300 ml of diethyl ether
  2. customThe combined organic phases are dried on magnesium sulfate
  3. customevaporated to the dry state in a vacuum
  4. customThe residue is chromatographed on silica gel (mobile solvent: n-hexane/diethyl ether 20:1)

Sources & evidence

ORD record
ord-a54ddf689e8c440b974add3452e5d5e0
Source dataset
uspto-grants-2004_11
Patent number
US06818203B2

Reaction notes

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