Acetic Acid → HCID 59595154, compound

HRID 2263636Notes

Reaction equation

HRID 2263636 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].[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](/[C:9](=[CH:26]\[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)/[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77254-MethylbenzaldehydeHCID 8082PiperidineHCID 16125894Tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate

Product 1

HCID 59595154HCID 59595154, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to general procedure A using tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate (18) (354 mg, 1.5 mmol), p-tolualdehyde (150 μL, 1.5 mmol), 15.0 mL benzene, piperidine (15 μL, 0.15 mmol) and glacial acetic acid (8.6 μL, 0.15 mmol), refluxed for 3 h. Purified via recrystallization from hexanes/CH2Cl2, yielding 350 mg (69%) of clear prisms. mp=86-89° C.; IR (film) 2978.2; 1712.8; 1624.5; 1155.2 cm−1; 1H NMR (100.7 MHz, CDCl3) δ 11.93 (bs, 1H), 7.82 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.48 (t, J=8.2 Hz, 1H), 7.25-7.08 (AA′BB′, 4H), 7.03 (d, J=8.2 Hz, 1H), 6.81 (t, J=7.6 Hz, 1H), 2.30 (s, 3H), 1.40 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 202.0, 163.9, 162.8, 142.3, 141.3, 137.1, 131.9, 130.4 (x2), 130.1, 129.9, 120.2, 119.5, 118.4, 82.6, 28.1, 21.6; LRMS (electrospray): Mass calculated for C21H22O4, [M]+, 338.14. Found [M+23]+, 361.4.

Workup

  1. customPrepared
  2. temperaturerefluxed for 3 h
  3. customPurified via recrystallization from hexanes/CH2Cl2

Sources & evidence

ORD record
ord-e4e0c286ef134391abe078ce8267519b
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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