Hydrochloric Acid → HCID 19067317, compound

HRID 481816

Reaction equation

HRID 481816 reaction equation
Cl[P:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[O:3]1.[C:16]1([Mg]Br)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.O.Cl>CC1C=CC=CC=1C.O1CCCC1>[OH:3][C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[P:2]([C:24]1[C:25]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][CH:23]=1)[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178418298HCID 178418298, compound

Product 1

HCID 19067317HCID 19067317, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Procedure

14.1 g (60 mmol) of 6-chloro-6H-dibenz[c,e][1,2]-oxaphosphorine in 50 ml of anhydrous o-xylene are introduced, in an argon atmosphere with stirring, and a solution of 150 mmol of 1-naphthylmagnesium bromide in tetrahydrofuran is added dropwise. The temperature increases in the course of this from 25° to 45° C. The mixture is then stirred for 3 hours at 80° C. and 5 hours at 120° C. The mixture is cooled to room temperature and 100 ml of water are added. The mixture is neutralized with dilute hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and concentrated under reduced pressure. 19.0 g of colorless oil are obtained. By crystallization with methanol/water, 10:1, 22.8 g (89%) of colorless crystals having melting point 255° to 256° C. are obtained.

Workup

  1. temperatureThe temperature increases in the course of this from 25° to 45° C
  2. stirringThe mixture is then stirred for 3 hours at 80° C. and 5 hours at 120° C
  3. customthe organic phase is separated off
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01a57633005444b38d0d21b92fc20fa6
Source dataset
uspto-grants-1998_08
Patent number
US05789623

Linked notes

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