Ethyl Bromide → Diethyl 2-hydroxybenzene-1,4-dicarboxylate

HRID 260415

Reaction equation

HRID 260415 reaction equation
N12CCCNC1CCC[CH:3]=[CH:2]2.[OH:12][C:13]1[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16].Br[C:26]1C=C(C(O)=O)C=C[C:27]=1C(O)=O.BrCC>C1C=CC=CC=1>[OH:12][C:13]1[CH:21]=[C:20]([C:22]([O:24][CH2:26][CH3:27])=[O:23])[CH:19]=[CH:18][C:14]=1[C:15]([O:17][CH2:2][CH3:3])=[O:16]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 68513Bromoterephthalic acidHCID 972572-Hydroxyterephthalic acidHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-ene

Product 1

HCID 22401614Diethyl 2-hydroxybenzene-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

6.62 g of 1,8-diazabicyclo[5.4.0]undecene and 100 mL benzene were added to 3.76 g hydroxyterephthalic acid (synthesized from bromoterephthalic acid by a known method) and the mixture was heated. 6.76 g of bromoethane dissolved in 38 mL benzene was added dropwise in and the reaction mixture was heated under reflux for 19 hours. The salt product was filtered off, and purification by column chromatography then yielded 4.66 g diethyl hydroxyterephthalate.

Workup

  1. temperaturewas heated
  2. additionwas added dropwise in and the reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 19 hours
  5. filtrationThe salt product was filtered off
  6. custompurification by column chromatography

Sources & evidence

ORD record
ord-b3305a26870c4436b3ea5f4482976b00
Source dataset
uspto-grants-1996_06
Patent number
US05527862

Linked notes

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