2-Chloroethanol → Phenol, 4-[(2-chloroethyl)thio]-

HRID 845089Notes

Reaction equation

HRID 845089 reaction equation
[Cl:1][CH2:2]CO.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]#N)=[CH:8][CH:7]=1.C(P(CC)CC)C>CC(C)=O.O.C(OCC)C>[Cl:1][CH2:2][CH2:13][S:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 342-ChloroethanolHCID 27365TriethylphosphineHCID 2203274-Hydroxyphenyl thiocyanate

Product 1

HCID 13576289Phenol, 4-[(2-chloroethyl)thio]-

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2-chloro-ethanol (3.9 g, 0.049 mole) was added to a solution of the product of Example 35 (7.4 g, 0.049 mole) in water (0.1 mole) and acetone (50 ml). After cooling with an ice bath triethylphosphine (5.6 g, 0.047 mole) was added dropwise over 25 minutes. Ethyl ether (200 ml) and water (75 ml) were added and the layers separated. The organic layer was washed with water (4×50 ml) and saturated sodium chloride (2×25 ml) dried over magnesium sulfate, filtered and concentrated to give a yellow oil. The structure was confirmed by its NMR spectrum.

Workup

  1. additionwas added dropwise over 25 minutes
  2. customthe layers separated
  3. washThe organic layer was washed with water (4×50 ml) and saturated sodium chloride (2×25 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-3709ffa22d0d4450bea236aa4ebfb0cf
Source dataset
uspto-grants-1988_07
Patent number
US04755524

Reaction notes

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