Hydrochloric Acid → Benzyl 5-hydroxypent-2-ynoate

HRID 1862435Notes

Reaction equation

HRID 1862435 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-093ea759939e4b6b8ab2ff8c8608d89a
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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