Water → HCID 86657468, compound

HRID 1408303Notes

Reaction equation

HRID 1408303 reaction equation
C[O:2][C:3](=O)[C:4]1C=C[C:7]([C:8](O)=O)=[CH:6][CH:5]=1.CCCC([O:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1Br)=[O:23])CC.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:3]([O:2][C:27]1[CH:26]=[CH:25][C:24]([C:22](=[O:23])[CH2:21][OH:20])=[CH:29][CH:28]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15513Monomethyl terephthalateHCID 67381962HCID 67381962, compound

Product 1

HCID 86657468HCID 86657468, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of terephthalic acid monomethyl ester (1.0 g, 5.6 mmol) and 4-hexyloxy-2′-bromoacetophenone (synthesized by following (2.0 g, 6.7 mmol) in DMF (10 mL) was added K2CO3 (0.77 g, 5.6 mmol) and heated at 60° C. After 10 h, the reaction mixture was cooled to room temperature and poured into water. The product was extracted using EtOAc, washed with brine, dried and concentrated. The crude residue was purified by combiflash to afford 1.0 g (45%) product. 1H NMR (500 MHz, CDCl3): δ 0.94 (t, 3H, J=7.0 Hz), 1.36-1.39 (m, 4H), 1.48-1.58 (m, 2H), 1.81-1.85 (m, 2H), 3.99 (s, 3H), 4.07 (t, 2H, J=6.5 Hz), 5.58 (s, 2H), 6.99 (d, 2H, J=9.0 Hz), 7.92 (d, 2H, J=9.0 Hz), 8.16 (d, 2H, J=9.0), 8.122 (d, 2H, J=9.0 Hz).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude residue was purified by combiflash

Sources & evidence

ORD record
ord-26ea46216e3640e08ca3806606c6e31a
Source dataset
uspto-grants-2014_12
Patent number
US08921309B2

Reaction notes

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