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Hydrochloric Acid → 2-Indancarboxylic Acid

HRID 1385065
Notes
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Reaction equation

HRID 1385065 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1(C(O)=O)[C:10]([OH:12])=[O:11].Cl.CCOCC>CN1C(=O)CCC1.O>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[C:10]([OH:12])=[O:11]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 2519571,3-Dihydroindene-2,2-dicarboxylic acid

Product 1

HCID 5757772-Indancarboxylic AcidYield 35.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of indane-2,2-dicarboxylic acid (17 g, Baeyer and Perkin, Ber. 1884, 17, 122) in NMP (200 ml) was heated to 150° C. for 1 hour. After cooling to 20° C. the solution was poured in water (300 ml) and concentrated hydrochloric acid was added to pH=1. Conventional work up with ether gave the title product (4.7 g). Mp 132-33° C. (from ether).

Sources & evidence

ORD record
ord-3ca22b31d0584613a61ea44396cdfdf6
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06262087B1

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes