Hydrochloric Acid → 40500-07-0

HRID 1743752Notes

Reaction equation

HRID 1743752 reaction equation
[OH-].[Li+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([O:13]C)=[O:12].Cl>O1CCCC1>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11095085HCID 11095085, compound

Product 1

HCID 2223651840500-07-0Yield 108.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of lithium hydroxide (4 mL of 2 M) was added to a solution of methyl 3-(tetrahydro-2H-pyran-2-yl)propionate (Preparation 5, 0.46 g, 2.67 mmol) in tetrahydrofuran (16 mL) and the reaction mixture was heated under reflux for 10 h. The cooled reaction mixture was acidified with aqueous 2N hydrochloric acid to pH 1, and then extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a colourless oil (460 mg, 67%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 10 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined extracts were washed with brine (30 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db4df99109974cbbbaadd1768aaa6b15
Source dataset
uspto-grants-2006_03
Patent number
US07012083B2

Reaction notes

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