Ethylene Oxide → 2,2'-((1,1'-Biphenyl)-4,4'-diylbis(oxy))bisethanol

HRID 1723270Notes

Reaction equation

HRID 1723270 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:17]1[O:19][CH2:18]1.C[O:21][CH2:22][CH2:23]OCCOC>>[OH:21][CH2:22][CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:18][CH2:17][OH:19])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6354Ethylene OxideHCID 71124,4'-DihydroxybiphenylHCID 8150DiglymeHCID 14798Sodium Hydroxide

Product 1

HCID 887492,2'-((1,1'-Biphenyl)-4,4'-diylbis(oxy))bisethanol

Procedure

1.5 mol (280 g) of 4,4'-dihydroxybiphenyl is dissolved in 1,263 g of diethylene glycol dimethyl ether and, after adding catalytic amounts of sodium hydroxide, oxethylated with ethylene oxide in the manner described in Example 2.1 at 170° C. to obtain 4,4'-bis(2-hydroxyethoxy)biphenyl. After subjecting the reaction mixture to an analogous working up step, the diol is obtained, mp 201°-202° C. (from tetrahydrofuran/cyclohexanone). The 1H NMR spectrum confirms the constitution of the diol.

Workup

  1. customdescribed in Example 2.1 at 170° C.

Sources & evidence

ORD record
ord-cfa572ed1be1477ba9e98397e041ae09
Source dataset
uspto-grants-1989_08
Patent number
US04859790

Reaction notes

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