Sodium Carbonate → 1-(4-Hydroxyphenyl)-1-(4-cyanatophenyl)-cyclohexane

HRID 1439535Notes

Reaction equation

HRID 1439535 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:21]#[C:22]Cl.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>O.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:22]#[N:21])=[CH:18][CH:19]=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 10477Cyanogen ChlorideHCID 14798Sodium HydroxideHCID 2324461,1-Bis(4-hydroxyphenyl)cyclohexane

Product 1

HCID 213958671-(4-Hydroxyphenyl)-1-(4-cyanatophenyl)-cyclohexaneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

86.8 g (0.1 mol) of 1,1-bis-(4-hydroxyphenyl)-cyclo hexane are suspended in 500 ml of water and 300 ml of methylene chloride at about 0° to 3° C. 20 ml (0.4 mol) of cyanogen chloride are added to this suspension and a solution of 10.6 g (0.1 mol) of Na2CO3 in 50 ml of water is added dropwise over the course of 90 minutes at the same temperature, with vigorous stirring, in such a way that a pH value between 7.5 and 8.5 is maintained in the reaction mixture. Thereafter, 1 N NaOH is added at 0° C in such a way that the abovementioned pH value is maintained, and persists as the final value. Thereafter, the organic phase is separated off and washed with 50 ml of water and the solvent is stripped off at room temperature. 29 g (99% of theory) of 1-(4-hydroxyphenyl)-1-(4-cyanatophenyl)-cyclohexane are thus obtained.

Workup

  1. customat about 0° to 3° C
  2. temperaturein such a way that a pH value between 7.5 and 8.5 is maintained in the reaction mixture
  3. temperatureis maintained
  4. customThereafter, the organic phase is separated off
  5. washwashed with 50 ml of water
  6. customis stripped off at room temperature

Sources & evidence

ORD record
ord-2448ea548d0c4864876da647f0934506
Source dataset
uspto-grants-1977_11
Patent number
US04060541

Reaction notes

Loading…