4-Hydroxy-5-methoxy-1,3-benzenedicarboxaldehyde → 1,2-Dihydroxy-3,5-diformylbenzene

HRID 1088893

Reaction equation

HRID 1088893 reaction equation
[OH:1][C:2]1[C:9]([O:10]C)=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH:12]=[O:13].P(Br)(Br)Br>ClCCl>[OH:1][C:2]1[C:9]([OH:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 180354-Hydroxy-5-methoxy-1,3-benzenedicarboxaldehydeHCID 24614Phosphorus tribromide

Product 1

HCID 190698721,2-Dihydroxy-3,5-diformylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension containing 1.8 g of 4-hydroxy-5-methoxyisophtalaldehyde in 20 ml of dichloromethane was added 35 ml of 1 molar PBr3 in dichloromethane. The mixture was allowed to stand over night at room temperature and poured the to ice-water. Dichloromethane was evaporated in vacuo. After cooling the product was filtered and washed with water. Yield 0.94 g (57%), m.p. 192°-195° C.

Workup

  1. waitto stand over night at room temperature
  2. customDichloromethane was evaporated in vacuo
  3. temperatureAfter cooling the product
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-0adebcea7bd546ad850129d98810c028
Source dataset
uspto-grants-1990_10
Patent number
US04963590

Linked notes

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