Sodium Hydroxide → 1-Indanacetic acid, 3-phenyl-

HRID 1389824Notes

Reaction equation

HRID 1389824 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([CH2:16][C:17]([O:19]CC)=[O:18])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([CH2:16][C:17]([OH:19])=[O:18])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12565675Ethyl 3-phenylindan-1-acetate

Product 1

HCID 30549451-Indanacetic acid, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Phenyl-1-indanone (83 g, 0.4 mol) was dried by refluxing in C6H6 (120 ml) with removal of the azeotroped H2O. To this solution was added Et2O (120 ml) and Zn wool (26.25 g, 0.4 mol). The reaction mixture was heated to near reflux and a crystal of I2 added. Ethyl bromoacetate (110 g, 0.6 mol) was added over 2 hours, the temperature being kept near reflux by heat of reaction and some external heating. After the addition, the mixture was stirred and refluxed for a further 0.5 hour, cooled and poured into ice and acetic acid. The mixture was extracted with Et2O. The Et2O was washed with 1% NH4OH, dried (Na2SO4), filtered and evaporated and the residue distilled to give a mixture of ethyl 3-phenylindene-1-acetate and its corresponding double bond isomer (83.6g) b.p. 145°-155° C. (0.1 mm). This mixture of esters was hydrogenated over 10% Pd/C (0.6g) to give ethyl 3-phenylindan-1-acetate. This ester was hydrolyzed by refluxing with sodium hydroxide in ethanol to give the title compound, m.p. 126°-9° C.

Sources & evidence

ORD record
ord-ab04a0802b2645b881362a1a49332acd
Source dataset
uspto-grants-1981_01
Patent number
US04246281

Reaction notes

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