Sulfuric Acid → HCID 21539606, compound

HRID 1076256Notes

Reaction equation

HRID 1076256 reaction equation
Cl[N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH3:13][C:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)([CH3:17])[CH2:15][OH:16]>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].O>[CH3:17][C:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([N:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)([CH3:13])[CH2:15][OH:16]

Participants

6

Reactant 3

HCID 1118Sulfuric Acid2×HCID 16540N-ChloropiperidineHCID 21539615HCID 21539615, compound

Product 1

HCID 21539606HCID 21539606, compound

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 962WaterSolvent

Procedure

Under agitation, a solution of 12 g. of N-chloropiperidine in 15 ml. of concentrated sulfuric acid is added dropwise within 10 minutes to a mixture of 24.2 g. of 2-methyl-2-(4-phenylphenoxy)-propanol (obtainable from 4-hydroxy-diphenyl and 2-bromo-2-methylpropanol), 7 g. of iron(II) sulfate heptahydrate, 8 ml. of concentrated sulfuric acid, and 3 ml. of water. The mixture is agitated for 15 minutes at 20°, then poured on ice water, washed with ether, made alkaline with sodium hydroxide solution, and extracted with chloroform. From the extract, after evaporation, one obtains 2-methyl-2-[4-(4-piperidinophenyl)-phenoxy]-propanol, m.p. 158°-160°.

Workup

  1. additionpoured on ice water
  2. washwashed with ether
  3. extractionextracted with chloroform
  4. customFrom the extract, after evaporation, one

Sources & evidence

ORD record
ord-b97d8427b92446bbb5c5adbcd8e00ded
Source dataset
uspto-grants-1976_05
Patent number
US03956334

Reaction notes

Loading…