Hydrochloric Acid → HCID 89975555, compound

HRID 716150Notes

Reaction equation

HRID 716150 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[O:8][C:7](=[O:9])[CH2:6][CH:5]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[Ca+2].[Cl-].Cl>C(O)C.O1CCCC1.C(OCC)(=O)C>[C:10]1([CH:5]([CH:4]([OH:8])[CH3:3])[CH2:6][CH2:7][OH:9])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 13403358HCID 13403358, compound

Product 1

HCID 89975555HCID 89975555, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.64 g of sodium tetrahydroborate was added to a solution of 1.2 g of 5-methyl-4-phenyloxolane-2-one in 2 mL of ethanol and 20 mL of tetrahydrofuran in a nitrogen atmosphere at a temperature of 5° C. to 10° C., and thereafter, a solution of 2.0 g of calcium chloride in 8 mL of ethanol was added dropwise to the mixture. The obtained mixture was stirred at room temperature for 200 minutes. Thereafter, 30 mL of ethyl acetate was added to the reaction mixture, and thereafter, 20 mL of 3 mol/L hydrochloric acid was added dropwise to the mixture. The organic layer was fractionated, and it was washed with a saturated sodium hydrogen carbonate aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 1.05 g of 3-phenylpentane-1,4-diol in the form of a colorless oily product.

Workup

  1. washit was washed with a saturated sodium hydrogen carbonate aqueous solution
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-f959070190024473a28049d0e919dadb
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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