Hydrochloric Acid → 2-Hydroxy-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide

HRID 29126Notes

Reaction equation

HRID 29126 reaction equation
[OH-].[Na+].Cl[P:4]1(=[O:22])[O:9][CH:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]([CH3:21])([CH3:20])[CH2:6][O:5]1.Cl.CC[O:26]CC>O>[OH:26][P:4]1(=[O:22])[O:9][CH:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]([CH3:21])([CH3:20])[CH2:6][O:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 225011462-Chloro-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide

Product 1

HCID 102825122-Hydroxy-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxideYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydroxide (29.4 g, 0.735 mol) was dissolved in water (300 ml). To the solution was added 2-chloro-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide (76.1 g, 0.245 mol) little by little, with stirring and heating at 100° C. The addition was completed for 35 min, and the solution was further stirred for 20 min. The reaction solution was cooled to 55° C., which resulted in precipitation of a large amount of crystals. Under stirring, concentrated hydrochloric acid (73 ml) was added to the mixture to adjust the mixture to acidic, and the mixture solidified and turned into powder by leaving it for about 1 hr. To the powder was added ether (100 ml), and the mixture was stirred and filtered. The obtained crystals were washed alternately with water and ether and dried to give the title compound as pale ocher crystals having the melting point of 216 to 217° C. (41.23 g, yield 57.6%).

Workup

  1. additionThe addition
  2. stirringthe solution was further stirred for 20 min
  3. temperatureThe reaction solution was cooled to 55° C.
  4. customwhich resulted in precipitation of a large amount of crystals
  5. stirringUnder stirring
  6. customby leaving it for about 1 hr
  7. stirringthe mixture was stirred
  8. filtrationfiltered
  9. washThe obtained crystals were washed alternately with water and ether
  10. customdried

Sources & evidence

ORD record
ord-b15f96923ebe4fe2a2dcdb295045e016
Source dataset
uspto-grants-2008_09
Patent number
US07420070B2

Reaction notes

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