Benzaldehyde → Homophthalic anhydride

HRID 397017Notes

Reaction equation

HRID 397017 reaction equation
N[CH2:2][C:3]([OH:5])=[O:4].[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.COC(OC)OC>CN(C=O)C.C(N(CC)CC)C>[C:3]1(=[O:4])[O:5][C:6](=[O:13])[C:7]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:8]2[CH2:2]1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 750GlycineHCID 9005Trimethyl orthoformate

Product 1

HCID 12801Homophthalic anhydride

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

The teabag containing glycine on resin was placed in a 20 mL bottle and treated with a solution of benzaldehyde (0.508 mL, 5 mmoles) and anhydrous trimethylorthoformate (1.094 mL, 10 mmoles) in anhydrous DMF (9 mL). After shaking for 3 hours, the packet was washed with anhydrous DMF (3×8 mL). A solution of homophthalic anhydride (801 mg, 5 mmoles) and triethylamine (0.044 mL, 0.3 mmoles) was prepared in DMF (10 mL) and added to the teabag. After shaking at room temperature for 16 hours the packet was washed with DMF (6×30 mL) and DCM (4×30 mL) and dried at room temperature.

Workup

  1. washthe packet was washed with anhydrous DMF (3×8 mL)
  2. additionadded to the teabag
  3. stirringAfter shaking at room temperature for 16 hours the packet
  4. washwas washed with DMF (6×30 mL) and DCM (4×30 mL)
  5. customdried at room temperature

Sources & evidence

ORD record
ord-3b6a0c2360084fd1a1560d18c35fdb47
Source dataset
uspto-grants-2003_08
Patent number
US06608082B1

Reaction notes

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