Hydrochloric Acid → HCID 86735500, compound

HRID 616815Notes

Reaction equation

HRID 616815 reaction equation
[CH2:1]([O:19][P:20]([CH2:41][C:42]1[CH:47]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:45]([OH:52])=[C:44](C(C)(C)C)[CH:43]=1)(=[O:40])[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[ClH:57]>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:19][P:20]([CH2:41][C:42]1[CH:47]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:45]([OH:52])=[C:44]([Cl:57])[CH:43]=1)(=[O:40])[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 76586Phosphonic acid, [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-, dioctadecyl ester

Product 1

HCID 86735500HCID 86735500, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

80.5 g of 3,5-di-tert. butyl-4-hydroxybenzyl-phosphonic acid di-n-octadecyl ester are dissolved in 250 ml of carbon tetrachloride and the solution is treated briefly with hydrogen chloride gas. The chlorination is effected by carefully bubbling in 10.5 g of chlorine gas for 3 hours at -5° C. The reaction mixture is allowed to come to room temperature and after stirring for a further 3 hours the solvent is removed in vacuo. The oily residue is digested with acetonitrile to purify the reaction product and the cyrstalline precipitate is isolated. The product is further purified by recrystallisation from aqueous ethylene glycol monomethyl ether. The resultant 3-chloro-5-tert. butyl-4-hydroxybenzyl-phosphonic acid di-n-octadecyl ester (stabiliser 3) forms white crystals with a melting point of 55° C.

Workup

  1. customby carefully bubbling in 10.5 g of chlorine gas for 3 hours at -5° C
  2. customto come to room temperature
  3. customis removed in vacuo
  4. customto purify the reaction product
  5. customthe cyrstalline precipitate is isolated
  6. customThe product is further purified by recrystallisation from aqueous ethylene glycol monomethyl ether

Sources & evidence

ORD record
ord-ad33874f5cca46f392918ce35a239b47
Source dataset
uspto-grants-1978_02
Patent number
US04076690

Reaction notes

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