Citric Acid → HCID 19375135, compound

HRID 128810Notes

Reaction equation

HRID 128810 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:19][O:18][CH:17]([O:20][CH3:21])[CH2:16][S:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 2401474-Mercaptophenol

Product 1

HCID 19375135HCID 19375135, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-mercaptophenol (3.81 g) in DMF (80 ml) is added potassium carbonate (8.3 g) and 1-bromo-2,2-dimethoxyethane (3.55 g). The mixture is stirred at 70° under nitrogen for 2 hr, then cooled and poured into 0.1N citric acid (600 ml). The product is extracted with ether, and the ether extracts are concentrated and distilled in vacuo (140°-145°, 0.01 torr), to provide 4-((2,2-dimethoxyethyl)thio)phenol as a pale yellow viscous oil (5.21 g, 81%).

Workup

  1. temperaturecooled
  2. extractionThe product is extracted with ether
  3. concentrationthe ether extracts are concentrated
  4. distillationdistilled in vacuo (140°-145°, 0.01 torr)

Sources & evidence

ORD record
ord-f6ed96d6130f4012adad1d01ae22014d
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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