Phenolphthalein → Calcium Bromide

HRID 1756259Notes

Reaction equation

HRID 1756259 reaction equation
[Br:1][CH:2]([C:6]([OH:8])=[O:7])[C:3]([OH:5])=[O:4].[OH-].[Ca+2:10].[OH-].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.[O:36]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49][O:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.O[CH:55]([C:59]([O-:61])=[O:60])[C:56]([O-:58])=[O:57].[Ca+2]>O>[Ca:10].[C:3]([CH:2]([C:6]([OH:8])=[O:7])[N:51]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][N:42]([CH:55]([C:59]([OH:61])=[O:60])[C:56]([OH:58])=[O:57])[CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:53][CH2:52]1)([OH:5])=[O:4].[Br-:1].[Ca+2:10].[Br-:1]

Participants

8

Reactant 5

HCID 4764PhenolphthaleinHCID 72805Diaza-18-crown-6HCID 521911Bromomalonic acidHCID 6093208Calcium Hydroxide2×HCID 19917397Calcium hydroxymalonate

Product 2

HCID 5360316Calcium BromideHCID 67782167N,N'-bis(dicarboxymethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane calcium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

After neutralizing 1.743 g (9.53 mmol) of 2-bromomalonic acid in 2.0 ml of water by adding calcium hydroxide in portions in the presence of phenolphthalein indicator, 1.000 g (3.81 mmol) of 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane is added. The reaction mixture is heated at 40°, 45° and finally at 50° C. for a total of 72 hours, then the reaction mixture is heated at 60° C. for 24 hours while portionwise adding 0.85 g (11.47 mmol) of calcium hydroxide under vigorous stirring. Then, the precipitate (the major part of which is calcium hydroxymalonate) is filtered off and washed with 4 to 5 ml of water in 3 portions. The combined filtrate is evaporated under reduced pressure and then 2×35 ml of methylene chloride are distilled off from the evaporation residue to obtain a solid product which is dried at 75° to 85° under reduced pressure. In this way the title product is obtained in a yield of 2.710 g (89.7%) with a calcium bromide content of 31.5% by weight.

Workup

  1. additionis added
  2. temperaturethe reaction mixture is heated at 60° C. for 24 hours
  3. filtrationis filtered off
  4. washwashed with 4 to 5 ml of water in 3 portions
  5. customThe combined filtrate is evaporated under reduced pressure
  6. distillation2×35 ml of methylene chloride are distilled off from the evaporation residue
  7. customto obtain a solid product which
  8. customis dried at 75° to 85° under reduced pressure

Sources & evidence

ORD record
ord-10bc62656842423788e090fee4a709af
Source dataset
uspto-grants-1995_08
Patent number
US05440031

Reaction notes

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