Hydrochloric Acid → HCID 68749089, compound

HRID 1912515Notes

Reaction equation

HRID 1912515 reaction equation
[CH3:1][C:2]1([CH3:11])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][SH:10].[OH-].[K+].Cl[CH:15]([CH3:19])[C:16]([OH:18])=[O:17].Cl>O>[CH3:1][C:2]1([CH3:11])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][S:10][CH:15]([CH3:19])[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 117342-Chloropropionic acidHCID 14797Potassium HydroxideHCID 76965285HCID 76965285, compound

Product 1

HCID 68749089HCID 68749089, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methanethiol (Eisen, Moris; et al. Inorg. Chim. Acta 1991, 188, 167-176) (52.0 g, 0.30 mmol) and potassium hydroxide (41.2 g, 0.62 mmol) in water (200 mL) was added α-chloro-propionic acid (33.2 g, 0.306 mmol) drop wise. The mixture was heated at 100° C. for 1 hour. The mixture was cooled and acidified to pH=1 with 6N HCl (100 mL). The product was extracted with ether, dried with magnesium sulfate and concentrated. The residue was distilled at reduced pressure (143-147° C., 0.5 mm of Hg) to obtain the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe product was extracted with ether
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. distillationThe residue was distilled at reduced pressure (143-147° C., 0.5 mm of Hg)

Sources & evidence

ORD record
ord-06b861e02a604b53b8ad48974244c0fb
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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