Acetic Anhydride → HCID 11806680, compound

HRID 1894915Notes

Reaction equation

HRID 1894915 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13].[C:19](OCC)(=[O:21])[CH3:20]>>[C:12]([O:1][C:2]1[CH:9]=[C:8]([O:10][C:19](=[O:21])[CH3:20])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5])(=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 68099Benzaldehyde, 2,4,6-trihydroxy-

Product 1

HCID 11806680HCID 11806680, compound

Procedure

2,4,6-Trihydroxybenzaldehyde (4) (4.62 g, 30 mmol), acetic anhydride (6.13 g, 60 mmol) and a catalytic amount of N,N-dimethylaminopyridine (DMAP) in dry ethyl acetate (EtOAc) (100 mL) were refluxed overnight. The reaction mixture was filtrated, water (50 mL) was added and the water phase extracted with EtOAc (4×25 mL). The combined organic phases were washed with water (2×25 mL) and dried (MgSO4). The crude product was recrystallized from 1,2-dimethoxyethane (DME) to give the titled compound as white crystals, m.p. 103-105° C. Yield 4.3 g. (60%). 1H NMR (300 MHz, CDCl3): δ=2.29 (3H, s), 2.36 (3H, s), 6.61 (1H, s), 6.63 (1H, s), 10.04 (1H, s), 11.77 (1H, s); 13C NMR (75 MHz): δ=20.6 (CH3), 21.0 (CH3), 107.6 (CH), 108.1 (CH), 111.0 (C), 153.5 (C), 157.2 (C), 163.9 (C), 169.7 (C═O), 168.1 (C═O), 191.8 (HCO).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. additionwater (50 mL) was added
  3. extractionthe water phase extracted with EtOAc (4×25 mL)
  4. washThe combined organic phases were washed with water (2×25 mL)
  5. dry with materialdried (MgSO4)
  6. customThe crude product was recrystallized from 1,2-dimethoxyethane (DME)

Sources & evidence

ORD record
ord-9c0dd0caa70f453fb2891e169a275609
Source dataset
uspto-grants-2013_08
Patent number
US08513395B2

Reaction notes

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