Thionyl Chloride → Diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)methylphosphonate

HRID 982042Notes

Reaction equation

HRID 982042 reaction equation
C(C1C=CC2C(C)(C)CCC(C)(C)C=2C=1)=O.O[CH:18]([P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1.S(Cl)([Cl:43])=O>>[Cl:43][CH:18]([P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 104208875,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehydeHCID 19786986Diethyl 1-hydroxy-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-methylphosphonate

Product 1

HCID 13604831Diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)methylphosphonateYield 88%

Procedure

216 g (1 mole) of 2-formyl-5,6,7,8-tetrahydro5,5,8,8-tetramethylnaphthalene were converted to 251 g (71%) of diethyl 1-hydroxy-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-methylphosphonate of melting point 93°-95° C., and 188.4 g (88%) of the title compound were obtained from 203 g (0.57 mole) of the lastmentioned compound and 287 ml of thionyl chloride. Since the material decomposes during distillation, the working up procedure was modified as follows. The crude product obtained after removal of the thionyl chloride was dissolved in toluene, and the solution stirred with 5 g of potassium carbonate for 20 minutes. The solid was filtered off, the solvent was removed and the solidified mass was comminuted in a mortar. The material thus obtained (m.p. 65°-66° C.) was about 85% pure according to the H-NMR spectrum. General method for the preparation of monoarylacetylenes.

Sources & evidence

ORD record
ord-fe6d55a473d54ba0b543ff9fb6463b5c
Source dataset
uspto-grants-1991_02
Patent number
US04994489

Reaction notes

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