p-Toluenesulfonic acid → 2-(4-Bromo-2-chlorophenoxy)methyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

HRID 77336

Reaction equation

HRID 77336 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[O:4]1.[Cl:21][C:22]1[CH:27]=[C:26]([Br:28])[CH:25]=[CH:24][C:23]=1O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:28][C:26]1[CH:25]=[CH:24][C:23]([O:1][CH2:2][CH:3]2[CH2:7][O:6][C:5]3([CH2:8][CH2:9][N:10]([CH2:13][CH2:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:11][CH2:12]3)[O:4]2)=[C:22]([Cl:21])[CH:27]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 198594-Bromo-2-chlorophenolHCID 667015182-Hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane2×

Product 1

HCID 510309912-(4-Bromo-2-chlorophenoxy)methyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decaneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (compound 1, 50 gm, 0.18 mole) was dissolved in toluene (300 ml) at room temperature. To this 44 gms of 2-chloro-4-bromophenol in toluene (150 ml) was added at room temperature 28° C. in the presence of ParaToluenesulfonic Acid (PTSA, 3.5 gm). Reaction mixture was refluxed with stirring for 13 hrs. It was then cooled and filtered. The filtrate was given water wash to bring the pH to neutral. Toluene was removed under vacuum to obtain a thick brick red colored product 95% yield.

Workup

  1. customReaction mixture
  2. temperaturewas refluxed
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. washwash
  6. customToluene was removed under vacuum

Sources & evidence

ORD record
ord-0b06f1d871e44007ad9e616efa9e2839
Source dataset
uspto-grants-2014_09
Patent number
US08841296B2

Linked notes

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