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

HRID 1679698Notes

Reaction equation

HRID 1679698 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].[OH-:20].[Na+].[CH2:22]=O.Cl>O>[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][C:3]1([CH2:18][CH3:19])[CH2:22][OH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 33794Acetic acid, 6,7-dichloro-2-ethyl-1-oxo-5-indanyloxy-

Product 1

HCID 20358453(1-Oxo-2-ethyl-2-hydroxymethyl-6,7-dichloro-5-indanyloxy)acetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (1-oxo-2-ethyl-6,7-dichloro-5-indanyloxy)acetic acid (3.03 g., 0.01 mole) and sodium hydroxide (0.5 g., 0.0125 mole) in water (90 ml.) is added aqueous formaldehyde (1 ml., 0.012 mole). The resulting solution is stirred at 20°-25° C. for 41/2 days and acidified with hydrochloric acid. The tan powder which precipitates is recrystallized from ethanol-water affording 1.2 g. of (1-oxo-2-ethyl-2-hydroxymethyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 155°-157° C.

Workup

  1. customThe tan powder which precipitates
  2. customis recrystallized from ethanol-water affording 1.2 g

Sources & evidence

ORD record
ord-2614de99a0a045ecb580b4d7f8b0332e
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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