Sulfuric Acid → 4-(2,4-Dichlorobenzyloxy)-phenethyl alcohol

HRID 435885

Reaction equation

HRID 435885 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].O[C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=1.S(=O)(=O)(O)O>C(O)C.O>[Cl:3][C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6][O:7][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10393TyrosolHCID 14798Sodium HydroxideHCID 156842,4-Dichlorobenzyl alcohol

Product 1

HCID 125273774-(2,4-Dichlorobenzyloxy)-phenethyl alcohol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.8 g. of sodium hydroxide in 10 ml. of water and 13.6 g. of 2,4-dichlorobenzyl alcohol are added to 8 g. of 4-hydroxyphenethyl alcohol in 80 ml. of ethanol. After refluxing the solution for 1.5 hours, the mixture is acidified with dilute sulfuric acid and extracted with methylene chloride. Drying and evaporation of the solvent yields the crude product at 100°-130° (air bath temperature)//0.02 torr by distillation with the use of a bulb tube. From cyclohexane, 14.5 g. of 4-(2,4-dichlorobenzyloxy)-phenethyl alcohol is obtained, m.p. 55°. The alcohol is converted, by 10 minutes of heating with thionyl chloride, into the [4-(β-chloroethyl)-phenyl]-(2,4-dichlorobenzyl)-ether and added to a solution of sodium imidazole, obtained by reacting 2 g. of imidazole with 1.04 g. of 80% strength sodium hydride - oil suspension in 30 ml. of dimethylformamide; the mixture is agitated for 6 hours at 100°-120° . The product is worked up as indicated in Example 56.

Workup

  1. temperatureAfter refluxing the solution for 1.5 hours
  2. extractionextracted with methylene chloride
  3. customDrying
  4. customevaporation of the solvent
  5. customyields the crude product at 100°-130° (air bath temperature)//0.02 torr
  6. distillationby distillation with the use of a bulb tube

Sources & evidence

ORD record
ord-6f4769142c504ab3a85006b598b6fe42
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Linked notes

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