Hydrochloric Acid → HCID 86093963, compound

HRID 2091485Notes

Reaction equation

HRID 2091485 reaction equation
C(O)(C)C.[BH4-].[Na+].[CH:7]([CH:9]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10][CH2:11][C:12](OC)=[O:13])=[O:8].Cl>O.CC(C)=O>[CH2:16]([CH:9]([CH2:10][CH2:11][CH2:12][OH:13])[CH2:7][OH:8])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 86094120HCID 86094120, compound

Product 1

HCID 86093963HCID 86093963, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

390.0 g of isopropanol and 22.4 g (0.59 mol) of sodium borohydride are placed in a one-liter round-bottomed flask with a magnetic stirrer, a thermometer and an addition funnel. 148.4 g (0.59 mol) of 91% methyl 4-formylundecanoate (6) are added dropwise over one hour. The temperature in the bulk rises to 35° C. during the addition. The addition is continued for 29 hours, while allowing the temperature in the bulk to return to room temperature (about 20° C.). After cooling the reaction medium to 5° C., 8.6 g of acetone are added, without exceeding 10° C. in the bulk. The reaction medium is again cooled to 5° C. and 240.0 g of hydrochloric acid are added over one hour, without exceeding 10° C. in the bulk. 250.0 g of water are added to facilitate the separation of the phases. The aqueous phase is extracted twice with 200 ml of toluene. The organic phases are combined and are washed once with 100.0 ml of water and once with 100 ml of brine. The resulting organic phase is dried over magnesium sulfate and filtered. The solvent is evaporated off under reduced pressure (3990 Pa) without exceeding 50° C. in the bulk. 118.0 g (0.42 mol) of 72% 2-heptylpentane-1,5-diol (10) are obtained, and are used directly in the cyclization step.

Workup

  1. additionThe temperature in the bulk rises to 35° C. during the addition
  2. additionThe addition
  3. customto return to room temperature
  4. custom(about 20° C.)
  5. customwithout exceeding 10° C. in the bulk
  6. temperatureThe reaction medium is again cooled to 5° C.
  7. customwithout exceeding 10° C. in the bulk
  8. customthe separation of the phases
  9. extractionThe aqueous phase is extracted twice with 200 ml of toluene
  10. washare washed once with 100.0 ml of water and once with 100 ml of brine
  11. dry with materialThe resulting organic phase is dried over magnesium sulfate
  12. filtrationfiltered
  13. customThe solvent is evaporated off under reduced pressure (3990 Pa)
  14. customwithout exceeding 50° C. in the bulk

Sources & evidence

ORD record
ord-d07bda9879284cf39cad9ba1a255d3bd
Source dataset
uspto-grants-2013_05
Patent number
US08440608B2

Reaction notes

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