m-Chloroperbenzoic acid → HCID 59822462, compound

HRID 595236Notes

Reaction equation

HRID 595236 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12](=[C:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH3:13]>ClCCl>[CH3:13][CH:12]1[C:14]2([CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[O:6]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22965782HCID 22965782, compound

Product 1

HCID 59822462HCID 59822462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperoxybenzoic acid (1.23 g, 7.13 mmol) was added to a solution of 4-ethylidenetetrahydro-2H-pyran (800 mg, 7.13 mmol) in dichloromethane (80 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for two hours. The mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate then saturated sodium thiosulfate. The layers were separated and the aqueous layer was re-extracted with dichloromethane (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 2-methyl-1,6-dioxaspiro[2.5]octane as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 3.88-3.76 (m, 4H), 2.92 (q, J=5.5 Hz, 1H), 1.91-1.81 (m, 2H), 1.58-145 (m, 2H), 1.30 (d, J=5.5 Hz, 3H).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. customThe layers were separated
  3. extractionthe aqueous layer was re-extracted with dichloromethane (2×)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7598a05c6744e7daa2f68140822316a
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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