Triethyl phosphite → Diethyl [(anthracen-9-yl)methyl]phosphonate

HRID 372565

Reaction equation

Cl[CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>CCCCCC>[CH:5]1[C:4]2[C:9](=[CH:10][C:11]3[C:16]([C:3]=2[CH2:2][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

After a mixture of 28.5g of 9-chloromethylanthracene and 62.3g of triethyl phosphite was heated at a temperature of 140° C for 2 hours with stirring, the mixture was cooled to a room temperature to obtain light yellowish needle-like crystalline product. The crystalline product was filtered off and washed with petroleum ether, and then dried. A crude product was obtained in a yield of 34.4g (83.8%). A pure crystalline product of diethyl 9-anthrylmethylphosphonate (m.p. 103.5° C - 104° C) was obtained by the recrystallization of the crude product from n-hexane in a yield of 31.2g.

Workup

temperaturethe mixture was cooled to a room temperature
customto obtain light yellowish needle-like crystalline product
filtrationThe crystalline product was filtered off
washwashed with petroleum ether
customdried
customA crude product was obtained in a yield of 34.4g (83.8%)

Sources & evidence

ORD record: ord-b94f661e9ace45cca1a8ecc30b420091
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04091208

Linked notes

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