Dichloromethane → 1,1-Bis (3-chloro-4-hydroxyphenyl)cyclododecane

HRID 980487Notes

Reaction equation

HRID 980487 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=C[CH:21]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:30])(=O)=O.[CH2:32]([Cl:34])Cl>>[Cl:30][C:3]1[CH:4]=[C:5]([C:8]2([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:32]([Cl:34])[CH:21]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24648Sulfuryl chlorideHCID 158500604,4'-(Cyclododecane-1,1-diyl)diphenol

Product 1

HCID 202217851,1-Bis (3-chloro-4-hydroxyphenyl)cyclododecane

Procedure

To a slurry containing 10 grams (0.0284 mole) of 1,1-bis(4-hydroxyphenyl)cyclododecane, prepared substantially in accordance with the procedure of Example 1, and 50 milliliters of methylene chloride, there is slowly added, at a temperature of 25°-27° C. and with stirring, a solution containing 26 grams (0.19 mole) of sulfuryl chloride and 20 milliliters of methylene chloride. During the addition of this solution the slurry turns to a solution. The reaction is followed by gas chromatographic analysis of samples removed from the reaction mixture. When analysis of these samples indicates the absence of the 1,1-bis(4-hydroxyphenyl)cyclododecane the solution is stripped on a rotary evaporator under water aspirator vacuum. Analysis of the solids indicates that they contain 93.6% of 1,1-bis(3-chloro-4-hydroxyphenyl)cyclododecane; 6% of 1-(4-hydroxyphenyl),1-(3-chloro - 4-hydroxyphenyl)cyclododecane; and 0.4% of 1-(3-chloro-4-hydroxyphenyl),1-(3,5-dichloro-4-hydroxyphenyl)cyclododecane. The solids are recrystallized from methanol to yield the pure 1,1- bis (3-chloro-4-hydroxyphenyl)cyclododecane, which has a melting point of 167°-169° C. and a gas chromatpgraphic retention time of 28.04 minutes relative to 13.97 minutes for p-cumyl phenol.

Workup

  1. additionis slowly added, at a temperature of 25°-27° C.
  2. additionDuring the addition of this solution the slurry
  3. customremoved from the reaction mixture
  4. customis stripped on a rotary evaporator under water
  5. customThe solids are recrystallized from methanol

Sources & evidence

ORD record
ord-cff5d54c78b2404683c9cb81441ca720
Source dataset
uspto-grants-1987_01
Patent number
US04638036

Reaction notes

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