Chloroform → HCID 737111, compound

HRID 492133Notes

Reaction equation

HRID 492133 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]12([OH:16])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.C(Cl)(Cl)Cl>>[Cl:1][CH2:2][C:3]([O:16][C:6]12[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2)=[O:4]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 6577Chloroacetyl chlorideHCID 641521-Adamantanol

Product 1

HCID 737111HCID 737111, compoundYield 37%

Procedure

At 10° C. and under N2, chloroacetyl chloride (9 mL, 113 mmol) was added slowly to a suspension of 1-adamantanol (11.4 g, 75 mmol) and MgO (4.5 g, 113 mmol) in CHCl3 (150 mmol). The mixture was heated to slight reflux for 43 h and cooled to RT. The insoluble material was removed by filtration and the solvent was evaporated. The residue was crystallized in hexanes to afford 2 as a white solid (6.324 g, 37%). U.S. Pat. No. 4,456,611; Helv. Chim. Acta 1988, 71, 1553.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto slight reflux for 43 h
  3. customThe insoluble material was removed by filtration
  4. customthe solvent was evaporated
  5. customThe residue was crystallized in hexanes

Sources & evidence

ORD record
ord-0bf014ddf40f49a493fc7352af1d04bd
Source dataset
uspto-grants-2009_05
Patent number
US07531662B2

Reaction notes

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