Hydrochloric Acid → HCID 23150319, compound

HRID 657651Notes

Reaction equation

HRID 657651 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:22]=[CH:21][C:9]([CH2:10][CH:11]2[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.Cl>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:22]=[CH:21][C:9]([CH2:10][CH:11]2[CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH2:12]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23150302HCID 23150302, compound

Product 1

HCID 23150319HCID 23150319, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-[4-(3-chloropropoxy)benzyl]-1,4-dioxaspiro[4.5]decane (630 mg) in a mixture of tetrahydrofuran (9.7 mL) and a 2N aqueous solution of hydrochloric acid (4.85 mL) is stirred for 20 h at room temperature, then concentrated under reduced pressure and diluted with ethyl acetate (10 mL) and alkalinized with an aqueous solution of sodium hydroxide. The organic phase is separated by decantation, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 546 mg of 4-[4-(3-chloropropoxy)benzyl]cyclohexanone used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with ethyl acetate (10 mL)
  3. customThe organic phase is separated by decantation
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bdaaa59fa1db4b78990979dd2d55fba0
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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