Benzoic Acid → Phthalide

HRID 839354Notes

Reaction equation

HRID 839354 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](N(CC)C1C=CC=C(N(CC)CC)C=1)C.C(OC(=O)C)(=O)C>CO>[C:1]1([C:2]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][O:9]1)=[O:8]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 7918Acetic AnhydrideHCID 19382815N~1~,N~1~,N~3~,N~3~-Tetraethylbenzene-1,3-diamine

Product 1

HCID 6885PhthalideYield 247.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
52 °C

Procedure

A mixture of 2-(4-dimethylamino)benzoyl)benzoic acid (8.07 g.), N,N,N',N'-tetraethyl-m-phenylenediamine (7.26 g.) and acetic anhydride (5 ml.) was heated (at 52° C.) during one and one-half hours. Addition of methanol (10 ml., then 15 ml.) afforded 3-(2,4-bis(diethylamino)phenyl)-3-(4-dimethylamino)phenyl)phthalide (I: X = (CH3CH2)2N, Y2 = Z4 = Z5 = Z6 = Z7 = H, Y4 = (CH3)2N) (10.92 g., m.p. 117°-119° C.).

Sources & evidence

ORD record
ord-7b4b6f615aef4c45a966df0a5f76aa2f
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Reaction notes

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