Acetic Acid → HCID 59595150, compound

HRID 2263638Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.N1CCCCC1.C(O)(=O)C>>[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1/[CH:21]=[C:9](\[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])=[O:17])/[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 69962-Chlorobenzaldehyde

HCID 8082Piperidine

HCID 16125894Tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate

Product 1

HCID 59595150HCID 59595150, compoundYield 20.1%

Procedure

Prepared according to general procedure A using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (236 mg, 1.0 mmol), 2-chlorobenzaldehyde (113 μL, 1.0 mmol) 15 mL benzene, piperidine (10 μL, 0.1 mmol) and glacial acetic acid (5.6 μL, 0.1 mmol), refluxed for 90 min. Purified via recrystallization from hexanes/CH2Cl2, yielding 72 mg (20%) of a white solid. mp=75-78° C. IR (film) 2979.0; 1720.5; 1630.9; 1156.3 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.80 (bs, 1H); 8.19 (s, 1H); 7.50 (d, J=7.9 Hz, 1H); 7.44 (t, J=7.9 Hz, 1H); 7.36 (d, J=7.9 Hz, 1H); 7.26 (d, J=7.9 Hz, 1H); 7.21 (t, J=7.6 Hz, 1H); 7.08 (t, J=7.06, Hz, 1H); 6.97 (d, J=7.9 Hz, 1H); 6.82 (t, J=7.6 Hz, 1H); 1.43 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 200.6, 163.3, 162.8, 139.1, 137.2, 135.0, 134.0, 131.9 (double intensity), 131.3, 130.2, 130.1, 127.2, 120.0, 119.5, 118.5, 83.1, 28.1; LRMS (electrospray): Mass calculated for C20H19ClO4 [M]+, 358.09. Found [M+23]+, 381.5.

Workup

customPrepared
temperaturerefluxed for 90 min
customPurified via recrystallization from hexanes/CH2Cl2

Sources & evidence

ORD record: ord-78df9f254b0f4c0a89f202a49771caa0
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851640B2

Reaction notes

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