Formaldehyde → Dibenzyl (hydroxymethyl)phosphonate

HRID 1517631Notes

Reaction equation

[P:1]([O-:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:19]=[O:20].C(N(CC)CC)C>>[CH2:3]([O:2][P:1]([CH2:19][OH:20])(=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 712Formaldehyde

HCID 8471Triethylamine

HCID 21904359Dibenzylphosphite

Product 1

HCID 14079960Dibenzyl (hydroxymethyl)phosphonateYield 42.5%

Procedure

Charged an Emrys 5 mL process vial with 2.0 g (7.63 mmol) dibenzyl phosphite, 229 mg (7.63 mmol) paraformaldehyde powder, and 0.11 mL (0.76 mmol) triethylamine. The white mixture was heated in a microwave (Personal Chemistry) at 130° for 5 minutes. The crude oil was purified on silica gel, eluting with 50-100% ethyl acetate in hexane to provide 947 mg (42% yield) of the title compound, a colorless oil. MS (ESI) m/z: 181.1, 293.0 [M+H]+ 1H NMR (DMSO-d6) δ: 3.83 (m, 2H), 5.02 (d, 4H), 5.50 (m, 1H), 7.37 (m, 10H).

Workup

temperatureThe white mixture was heated in a microwave (Personal Chemistry) at 130° for 5 minutes
customThe crude oil was purified on silica gel
washeluting with 50-100% ethyl acetate in hexane

Sources & evidence

ORD record: ord-369f57b198da45668c0095c8e1168e12
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232309B2

Reaction notes

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