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Acetic Anhydride → 7-Methoxyisochroman-1,3-dione

HRID 1182922
Notes
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Reaction equation

HRID 1182922 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[C:6](=[CH:11][CH:12]=1)[CH2:7][C:8]([OH:10])=O)[CH3:2].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[O:1]([C:3]1[CH:4]=[C:5]2[C:13](=[O:14])[O:15][C:8](=[O:10])[CH2:7][C:6]2=[CH:11][CH:12]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23054232-(carboxymethyl)-5-methoxybenzoic acid

Product 1

HCID 121967027-Methoxyisochroman-1,3-dioneYield 110.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.1 g (5.2 mmol) of 4-methoxylhomophthalic acid (IIb) was dissolved in 20 ml toluene, and 0.7 ml (7.9 mmol) of acetic anhydride was added. The mixture was heated to the reflux temperature and reacted for 0.5 h. Then, the reaction mixture was cooled to the room temperature and concentrated to dry in a reduced pressure to obtain 1.1 g of a pale yellow solid with the yield of 100%. m.p. 142-143° C.

Workup

  1. temperatureThe mixture was heated to the reflux temperature
  2. customreacted for 0.5 h
  3. concentrationconcentrated
  4. customto dry in a reduced pressure

Sources & evidence

ORD record
ord-0e854e3c0041495d83017d510ade7a4a
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664238B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes