Trimethyl phosphite → Phosphinecarboxylic acid, dimethoxy-, cyclohexyl ester, oxide

Reaction equation

C[O:2][P:3]([O:6][CH3:7])[O:4][CH3:5].[CH:8]1([O:14][C:15](Cl)=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([O:14][C:15]([P:3](=[O:2])([O:6][CH3:7])[O:4][CH3:5])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Reactant 2

HCID 8472Trimethyl phosphite

HCID 83262Carbonochloridic acid, cyclohexyl ester

Product 1

HCID 512109Phosphinecarboxylic acid, dimethoxy-, cyclohexyl ester, oxide

Procedure

From 24.8 g (0.20 mole) of trimethylphosphite and 32.1 g (0.20 mole) of cyclohexylchloroformate. (Y. Iwakura and A. Nabeya, J. Org. Chem. 25 (1960) 1118; M. E. Fourneau et al. Chem. Abstr. 16 (1922) 240; J. H. Saunders et al. J. Am. Chem. Soc. 73 (1951) 3797). (100° C., 2 hours). Yield 30 g (64%). Bp1.4-1.8 148°-151° C. nD21 1.4543.

Workup

custom(100° C., 2 hours)
customBp1.4-1.8 148°-151° C.

Sources & evidence

ORD record: ord-d9c6470e7d8542e8a26b078d80e40ed5
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04386081

Reaction notes

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