Water → HCID 90101567, compound

HRID 631765Notes

Reaction equation

[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].O>CCCCCC.CC(O)C>[C:11]([O:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:23][CH:22]=1)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

Polyphosphoric acid (PPA) (250 g) was charged to a reaction vessel and warmed to 50° C. (bath temperature) with mechanical stirring. 2-Phenylacetic acid (30.6 g, 0.225 mol) was added to PPA followed by 2-phenoxyethyl pivalate (50 g, 0.225 mol). After 3 hours TLC and HPLC indicated full conversion and water (1000 ml) was added. The mixture was stirred at room temperature for 2 h. The precipitated product was filtered and washed with water (300 ml). After drying in vacuo the crude product (65 g) was re-crystallized with hexane/i-PrOH 1:1 yielding the title compound as slightly yellow solid (51.49 g, 0.151 mol, 67%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.02 (2H, d, J=9.2 Hz, ArH), 7.32-7.22 (5H, m, ArH), 7.07 (2H, d, J=8.8 Hz, ArH), 4.37 (2H, m, CH2CH2OPiv), 4.31 (2H, s, ArCH2CO), 4.3 (2H, m, ArOCH2CH2), 1.12 (9H, s, 3×Me). 13C-NMR (100 MHz, DMSO-d6) δ (ppm): 196.4, 177.7, 162.6, 135.8, 131.2, 129.9, 129.8, 128.7, 126.8, 114.8, 66.5, 62.7, 44.8, 38.6, 27.2.

Workup

filtrationThe precipitated product was filtered
washwashed with water (300 ml)
dry with materialAfter drying in vacuo the crude product (65 g)

Sources & evidence

ORD record: ord-e9fd1fce30564be290aff7b902990709
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321712B2

Reaction notes

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