Hydrochloric Acid → HCID 22850937, compound

HRID 487217Notes

Reaction equation

HRID 487217 reaction equation
[Na].[CH3:2][C:3]1([CH3:13])[C@H:8]2[CH2:9][C@@H:4]1[CH2:5][CH2:6][C@H:7]2[CH2:10][CH2:11]Cl.Cl.[CH2:15]([OH:20])[CH2:16][CH2:17][CH2:18][OH:19]>>[CH3:2][C:3]1([CH3:13])[C@H:8]2[CH2:9][C@@H:4]1[CH2:5][CH2:6][C@H:7]2[CH2:10][CH2:11][O:19][CH2:18][CH2:17][CH2:16][CH2:15][OH:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 80641,4-ButanediolHCID 5360545SodiumHCID 22850931(1S,2S,5S)-2-(2-Chloroethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Product 1

HCID 22850937HCID 22850937, compound

Conditions

Temperature
130 °C

Procedure

12.2 g elemental sodium were dissolved in portions spread over 12 hours in 320 ml 1,4-butanediol at a temperature of 90° C. Then 80 g 2-((1S,2S,5S)-6,6dimethylbicyclo[3,1,1]hept-2-yl)-ethyl chloride were added in drops to this solution, and the reaction mixture was heated to 130° C. for 15 hours. In order to work up the reaction mixture it was cooled to room temperature, then 300 ml of a 5% aqueous hydrochloric acid solution were added, and the mixture was extracted with ether. After evaporation of the ether extract, 95.2 g crude 4-[2-((1S,2S,5S)-6,6dimethylbicyclo[3,1,1]hept-2-yl)-ethoxy]-butanol were obtained.

Workup

  1. temperaturewas cooled to room temperature
  2. extractionthe mixture was extracted with ether
  3. customAfter evaporation of the ether
  4. extractionextract

Sources & evidence

ORD record
ord-06e336b91a724d8eaa845f0949bb6a30
Source dataset
uspto-grants-1994_03
Patent number
US05294638

Reaction notes

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