Phosgene → Carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

HRID 1388493Notes

Reaction equation

HRID 1388493 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)([CH3:17])[CH3:16])=[CH:11][CH:10]=1.[OH-:25].[Na+].[C:27](Cl)(Cl)=[O:28]>C(Cl)Cl.O>[CH3:17][C:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[CH3:16].[C:27]([OH:28])([OH:8])=[O:25]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 6623Bisphenol A2×HCID 8471TriethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 159987Carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 1000 ml four neck flask was fitted with a mechanical stirrer, a pH probe, aqueous caustic inlet tube and a Claisen adapter to which was attached a dry ice condenser and a gas inlet tube. To the flask was added 280 ml water, 340 ml methylene chloride, 1.4 ml triethyl amine (0.01 mole) and 57 g (0.25 mole) bisphenol-A. With stirring the pH was raised to 10 by addition of 25% aqueous sodium hydroxide, then 0.00925 mole (3.7 mole%) based upon mole of BPA of the acid or acid chloride end-capping agent was added. Phosgene was introduced into the flask at 1 g/min for 30 minutes (0.3 mole) with pH maintained at 9.5 to 11.5. The pH was adjusted to 11 at the end of the reaction. The resin layer was separated from the brine layer, then washed with 3 wt. % aqueous HCl until washing remained acidic, then twice with distilled water. The resin was then precipitated into 1500 ml of methanol in a Waring blender and washed with 500 ml more methanol.

Workup

  1. additionwas added
  2. temperaturemaintained at 9.5 to 11.5
  3. customThe pH was adjusted to 11 at the end of the reaction
  4. customThe resin layer was separated from the brine layer
  5. washwashed with 3 wt. % aqueous HCl
  6. washuntil washing
  7. customThe resin was then precipitated into 1500 ml of methanol in a Waring blender
  8. washwashed with 500 ml more methanol

Sources & evidence

ORD record
ord-48b1768889364e2299d658f4206a60a3
Source dataset
uspto-grants-1984_02
Patent number
US04431793

Reaction notes

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