Phenylacetic Acid → Dimethyl phenylacetylphosphonate

HRID 1265955Notes

Reaction equation

C1(CC(O)=O)C=CC=CC=1.C[Si](C)(C)[C:13]1[CH:14]=[C:15]([CH2:19][C:20]([P:22](=[O:27])([O:25][CH3:26])[O:23][CH3:24])=[O:21])[CH:16]=[CH:17][CH:18]=1>>[C:15]1([CH2:19][C:20]([P:22](=[O:27])([O:23][CH3:24])[O:25][CH3:26])=[O:21])[CH:14]=[CH:13][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 999Phenylacetic Acid

HCID 11208811Dimethyl m-trimethylsilylphenylacetylphosphonate

Product 1

HCID 11075154Dimethyl phenylacetylphosphonate

Procedure

This compound was prepared from phenylacetic acid (0.68 g, 5.0 mmol) as described for the preparation of the trimethylsilyl analogue 50a. The reaction furnished 1.17 g of 50b as a white solid, mp. 117-122° C. (hygroscopic). IR (film): 3600-2600, 1457, 1312, 1237 and 1053; 1H NMR (200 MHz, CDCl3): δ3.83 (6H, d, J=11 Hz), 6.07 (1H, d, J=12 Hz) and 7.52 (5H, m); 13C NMR (50 MHz, CDCl3): δ53.6, 116.3, 116.8, 127.2, 127.3, 127.9, 129.2, 133.7, 134.1, 137.8 and 141.9; 31P (202 MHz; CDCl3; H3PO4): δ16.1; HR-MS (EI): mi/e 228.0550 (M+C10H13O4P requires 228.0551).

Sources & evidence

ORD record: ord-cb1745af0a7c491a9ca0fc398ead0067
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548042B2

Reaction notes

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