Hydrochloric Acid → Cyclohexanone, 4-[(phenylmethoxy)methyl]-

HRID 1043229Notes

Reaction equation

HRID 1043229 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:13]2(OCC[O:14]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>O1CCOCC1.[Cl-].[Na+].O.C(=O)(O)[O-].[Na+].CCOCC>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:11][CH2:12][C:13](=[O:14])[CH2:18][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 103780318-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 10443381Cyclohexanone, 4-[(phenylmethoxy)methyl]-

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of EXAMPLE 441C (43.02 g) in dioxane (500 mL) was added water (125 mL) and 2M hydrochloric acid (90 mL). The mixture was heated at 85° C. for 18 hours. Upon cooling, the reaction mixture was diluted with brine (1500 mL), saturated sodium bicarbonate solution (300 mL) and ether (1000 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified on silica gel eluting with a 5, 15, 25, 50% ethyl acetate in hexanes step gradient to give the title compound.

Workup

  1. temperatureUpon cooling
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on silica gel eluting with a 5, 15, 25, 50% ethyl acetate in hexanes step gradient

Sources & evidence

ORD record
ord-03779f683a544dd492349fc55e397889
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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