Ethanol → HCID 58248137, compound

HRID 1496824Notes

Reaction equation

HRID 1496824 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12].[CH2:14](O)[CH3:15]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

3

Reactant 2

HCID 702EthanolHCID 58248142HCID 58248142, compound

Product 1

HCID 58248137HCID 58248137, compoundYield 90%

Procedure

A solution of acrylic acid 8 (4.35 g, 18.0 mmol) in dry ethanol (50 mL) with a small quantity of acid resine DOWEX™ (300 mg) was refluxed for 24 h. The reaction mixture was filtered, the solvent was evaporated in vacuo and the crude reaction product was purificated by means of chromatography on silica gel (hexane/AcOEt 10:1) to give 4.36 g of ester 9 as a white solid. Yield 90%. 1H RMN (300 MHz, CD3COCD3) δ ppm: 8.82 (br s, 1H), 7.94 (d, J=16.1 Hz, 1H), 7.49 (d, J=8.7 Hz, 1H), 7.28 (d, J=2.9 Hz, 1H), 6.88 (dd, J1=8.7 Hz, J2=2.9 Hz, 1H), 6.45 (d, J=16.1 Hz, 1H), 4.24 (q, J=7.1 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H); 13C RMN (75 MHz, CD3COCD3) δ ppm: 167.5, 159.1, 144.0, 136.7, 135.9, 123.0, 121.3, 116.2, 115.8, 62.1, 15.6; HRMS (EI) m/z: calcd for C11H11BrO3: 269.9892. found: 269.9886; mp: 96-98° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated in vacuo
  3. customthe crude reaction product

Sources & evidence

ORD record
ord-d6e8474bc29847f7b8c13ef1bf58ac93
Source dataset
uspto-grants-2015_12
Patent number
US09199936B2

Reaction notes

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