Potassium Carbonate → 2-[(4-Chlorobutyl)thio]benzyl alcohol

HRID 1034164Notes

Reaction equation

HRID 1034164 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][Cl:21]>C(O)(C)C>[Cl:21][CH2:20][CH2:19][CH2:18][CH2:17][S:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 1382782-Mercaptobenzenemethanol

Product 1

HCID 540055542-[(4-Chlorobutyl)thio]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 5 liter 4-neck round-bottom flask fitted with mechanical stirrer, thermowell, and addition funnel, under a nitrogen atmosphere, was added 150.0 g of o-mercaptobenzyl alcohol, 2400 ml of isopropanol and 295.72 g of anhydrous potassium carbonate. The reaction mixture was cooled in an ice bath, as 246.6 ml of 1-bromo-4-chlorobutane was added dropwise. After addition was complete, the mixture was allowed to warm to room temperature, and stirred at room temperature overnight. The mixture was filtered through a pad of filter aid, and the solid was rinsed with fresh isopropanol. The solvent was removed by rotary evaporation to give 246.0 g of the product as a brown oil. 1H-NMR (CDCl3) δ 1.7-2.1(m,4H); 2.3(br s,1H); 2.85-3.0(t,2H); 3.5-3.6(t,2H); 4.75(s,2H); 7.2-7.4(m,4H).

Workup

  1. customTo a 5 liter 4-neck round-bottom flask fitted with mechanical stirrer
  2. additionthermowell, and addition funnel
  3. additionwas added dropwise
  4. additionAfter addition
  5. filtrationThe mixture was filtered through a pad of filter aid
  6. washthe solid was rinsed with fresh isopropanol
  7. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-5a24e86488e64243aa7b36ae1d754b25
Source dataset
uspto-grants-1994_05
Patent number
US05314887

Reaction notes

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