Hydrochloric Acid → Hydroxymethylphenylphosphinic acid

HRID 462811Notes

Reaction equation

HRID 462811 reaction equation
C([O:3][PH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])C.[CH2:12]=[O:13].Cl>>[OH:13][CH2:12][P:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[OH:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 178476779HCID 178476779, compound

Product 1

HCID 12062247Hydroxymethylphenylphosphinic acidYield 80.6%

Procedure

100 g (0.5 moles) of phenylphosphinic acid ethyl ester are heated to 80° C., and 15 g (0.52) of paraformaldehyde are added in small portions. The paraformaldehyde addition is regulated so that the temperature does not exceed 110° C. by virtue of the exothermic nature of the reaction. When the addition is complete, the mixture is kept for about one hour under agitation at 110° C., and the termination of the reaction can be seen by gas chromatography or thin layer chromatography. 100 cc of a 10% HCl solution are then added, and the mixture kept at 80° C. for 30 min. The water and hydrochloric acid are then evaporated under vacuum, and the mixture taken up in isopropanol. On cooling, 69.3 g of hydroxymethylphenylphosphinic acid are obtained with a yield of 80.5% and a melting point of 138°-9° C.

Workup

  1. customdoes not exceed 110° C. by virtue of the exothermic nature of the reaction
  2. additionWhen the addition
  3. customthe termination of the reaction
  4. waitthe mixture kept at 80° C. for 30 min
  5. customThe water and hydrochloric acid are then evaporated under vacuum
  6. temperatureOn cooling

Sources & evidence

ORD record
ord-02aa8a30bea64a36b255fc14984f7ec0
Source dataset
uspto-grants-1985_05
Patent number
US04517355

Reaction notes

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