Hydrochloric Acid → HCID 18651835, compound

HRID 248846Notes

Reaction equation

HRID 248846 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:21])[CH2:16][CH2:17][CH2:18][CH2:19][OH:20]>>[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:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][OH:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 81051,5-PentanediolHCID 5360545SodiumHCID 22850931(1S,2S,5S)-2-(2-Chloroethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Product 1

HCID 18651835HCID 18651835, compound

Conditions

Temperature
130 °C

Procedure

Over the course of 12 hours, 12.2 g of elemental sodium were dissolved in portions in 357 ml of 1,5-pentanediol at a temperature of 90° C. 80 g of 2-((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-y l)ethyl chloride were then added dropwise to this solution, and the reaction mixture was heated at 130° C. for 15 hours. The reaction mixture was worked up by cooling to room temperature, adding 300 ml of a 5% strength aqueous hydrochloric acid solution, and extracting the mixture with ether. After concentrating the ether extract, 99.6 g of crude 5-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl )ethoxy]pentanol were obtained.

Workup

  1. temperatureby cooling to room temperature
  2. extractionextracting the mixture with ether
  3. concentrationAfter concentrating the ether
  4. extractionextract

Sources & evidence

ORD record
ord-21c4763075184f22bcffbd56013b3465
Source dataset
uspto-grants-1993_05
Patent number
US05212173

Reaction notes

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