Hydrochloric Acid → HCID 76714893, compound

HRID 573496Notes

Reaction equation

HRID 573496 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH2:10][CH2:11][CH:12]=[CH:13][CH:14]=[CH:15][CH3:16])[CH2:5][C:6]([O:8][CH3:9])=[O:7].Cl>C1COCC1>[OH:3][CH:4]([CH2:10][CH2:11][CH:12]=[CH:13][CH:14]=[CH:15][CH3:16])[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 53968723Methyl 3-oxodeca-6,8-dienoate

Product 1

HCID 76714893HCID 76714893, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a stream of nitrogen, sodium borohydride (5.1 g, 0.14 mol) and THF (360 ml) were put into a 1-L flask, followed by cooling to 0° C. Methyl 3-oxo-6,8-decadienoate (f) (88.8 g, 0.45 mol) was added dropwise thereinto for 1 hour. After completion of the dropwise addition, a 35% aqueous solution of hydrochloric acid (47 g) was added dropwise thereinto, followed by extraction twice with ethyl acetate (180 ml). After the organic layer was washed with water (178 mL), the solvent was removed under a reduced pressure. Thus, methyl 3-hydroxy-6,8-decadienoate (g) was obtained (86.1 g, 0.43 mol, yield 96%).

Workup

  1. additionAfter completion of the dropwise addition
  2. extractionfollowed by extraction twice with ethyl acetate (180 ml)
  3. washAfter the organic layer was washed with water (178 mL)
  4. customthe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-592b4d85902e433faf3b9b6bcb03d374
Source dataset
uspto-grants-2015_05
Patent number
US09029593B2

Reaction notes

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