Hydrochloric Acid → (1-Hydroxy-2-ethyl-6,7-dichloro-5-indanyloxy)-acetic acid

HRID 596991Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH2:18][CH3:19].[BH4-].[K+].Cl>O>[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][CH:3]1[CH2:18][CH3:19]

Participants

Conditions

Temperature: 5 °C

Procedure

A stirred suspension of (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid (12.12 g., 0.04 mole) in water (400 ml.) is cooled to 5° C. and treated during a one hour period with solution of potassium borohydride (4.0 g., 0.075 mole) in water (200 ml.). The reaction is stirred for 1 hour then acidified with hydrochloric acid affording 10.6 g. (87%) of (1-hydroxy-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 121°-122° C. after recrystallization from benzene.

Workup

custom(87%) of (1-hydroxy-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 121°-122° C. after recrystallization from benzene

Sources & evidence

ORD record: ord-0b7634c582df427e9a27dc0fdb7718d7
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04012524

Reaction notes

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