Hydrochloric Acid → Benzyl 5-hydroxypent-2-ynoate

HRID 1837082Notes

Reaction equation

HRID 1837082 reaction equation
C(OC([O:6][CH2:7][CH2:8][C:9]#[C:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])C)C.Cl>CC(C)=O.O.C(OCC)(=O)C>[OH:6][CH2:7][CH2:8][C:9]#[C:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 23497522HCID 23497522, compound

Product 1

HCID 15073126Benzyl 5-hydroxypent-2-ynoateYield 100%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product from Example 31B (122.1 g, 0.442 mole) in acetone (400 mL) was treated at ambient temperature with an aqueous hydrochloric acid solution (0.5 N, 200 mL). The reaction mixture was stirred for 6 hours and then diluted with water and ethyl acetate. The layers were separated, and the organic layer was dried over magnesium sulfate, filtered and concentrated to provide the title compound as a colorless oil (90.17 g, 100%). 1H NMR (300 MHz, CDCl3) δ 2.61 (t, 2H), 3.79 (t, 2H), 5.19 (s, 2H), 7.32-7.40 (m, 5H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eb3ca62c71c241689a1f2bd6af3abc9e
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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