Hydrochloric Acid → 1-Propanol, 2-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 1655819Notes

Reaction equation

HRID 1655819 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH:14]([CH3:19])[C:15](OC)=[O:16].Cl>CCOCC>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH:14]([CH3:19])[CH2:15][OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13874081Methyl 2-tetrahydropyranyloxypropionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5591501-Propanol, 2-[(tetrahydro-2H-pyran-2-yl)oxy]-Yield 90.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

25.0 g of lithium aluminum hydride was suspended in anhydrous ether, and 36.7 g of the compound (5a) was added thereto, followed by stirring for 1 hour at 0° C. and 2 hours at room temperature and neutralization by addition of aqueous HCl solution at 0° C. The reaction mixture was subjected to extraction with ether and reduced pressure-distillation (60° C./0.3 mmHg) to obtain 28.0 g of the product. (Yield: 90.2 %)

Workup

  1. extractionThe reaction mixture was subjected to extraction with ether and reduced pressure-distillation (60° C./0.3 mmHg)

Sources & evidence

ORD record
ord-de6757c150474efaa75ad8bb4802a4a0
Source dataset
uspto-grants-1993_10
Patent number
US05252251

Reaction notes

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