Malonic Acid → 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

HRID 258186Notes

Reaction equation

HRID 258186 reaction equation
[CH2:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9](O)[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(O)(=O)[CH2:18][C:19]([OH:21])=[O:20]>>[CH:4]1[C:3]2[CH2:2][CH2:1][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:9]([CH2:18][C:19]([OH:21])=[O:20])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 14588Dibenzosuberol

Product 1

HCID 1266909110,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

Procedure

Thus, as outlined in Scheme III, dibenzosuberol (XVI) is heated with malonic acid to about 160° C. to afford 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (XV). A solution of the acid (XV) in a solvent such as, for example, ethylene glycol dimethyl ether and the like in the presence of a base such as, for example, N,N-diisopropylethylamine and the like is reacted with pivaloyl chloride to afford the mixed anhydride (XIV) in situ.

Sources & evidence

ORD record
ord-bf53a682da7240fc800b03b771518759
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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