2-Chloroethanol → Biphenol-diethanol

HRID 2248422Notes

Reaction equation

HRID 2248422 reaction equation
[C:1]1([OH:14])[C:2]([C:7]2[C:8]([OH:13])=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH-].[Na+].Cl[CH2:18][CH2:19][OH:20].[CH2:21]([OH:23])[CH3:22]>>[C:8]1([OH:13])[C:7]([C:2]2[C:1]([OH:14])=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:12]([CH2:22][CH2:21][OH:23])[C:11]([CH2:18][CH2:19][OH:20])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 342-ChloroethanolHCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

HCID 19996287Biphenol-diethanol

Procedure

To biphenol (0.5 mole) and 200 milliliters of absolute ethanol and sodium hydroxide (1.1 millimole) at 80° C. was added dropwise a solution of 2-chloroethanol (1 mole) in 50 milliliters of absolute ethanol. The mixture was refluxed for 48 hours, and then filtered hot and washed twice with boiling ethanol (100 milliliters). Recrystallization from boiling water provided the precursor product biphenol-diethanol, 80 to 85 percent yield of colorless crystals. The melting point for this product was 210° to 211° C.

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. filtrationfiltered hot
  3. washwashed twice with boiling ethanol (100 milliliters)
  4. customRecrystallization

Sources & evidence

ORD record
ord-070be18c99c144e291c36479ce60576c
Source dataset
uspto-grants-1991_08
Patent number
US05039773

Reaction notes

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