Benzyl iodide → 1,3,2-Dioxaphosphorinane, 5,5-dimethyl-2-(phenylmethyl)-, 2-oxide

HRID 904796Notes

Reaction equation

HRID 904796 reaction equation
C([O:8][P:9]1[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]1)C1C=CC=CC=1.[CH2:17](I)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C(C)=CC=CC=1>[CH2:17]([P:9]1(=[O:8])[O:10][CH2:11][C:12]([CH3:15])([CH3:16])[CH2:13][O:14]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 12098Benzyl iodideHCID 204776611,3,2-Dioxaphosphorinane, 5,5-dimethyl-2-(phenylmethoxy)-

Product 1

HCID 850841,3,2-Dioxaphosphorinane, 5,5-dimethyl-2-(phenylmethyl)-, 2-oxideYield 8,386.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-benzyloxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (100 g, 0.416 M) from Example II, benzyl iodide (1.0 g), and xylene (50 ml) was heated until the temperature reached 165° C., and then slowly dropped to 155° C. After 1.5 hrs, the mixture was allowed to cool to yield 92.4 g (92.4% yield) of pure crystalline 2-benzyl-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-one, melting point 109.5°-110.5° C. Analysis by gas-liquid chromatography showed no impurities present.

Workup

  1. temperaturewas heated until the temperature
  2. customreached 165° C.
  3. additionslowly dropped to 155° C
  4. temperatureto cool

Sources & evidence

ORD record
ord-607f84c0bf98496f828bb08acfed2e6c
Source dataset
uspto-grants-1983_12
Patent number
US04420437

Reaction notes

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