Sulfuric Acid → HCID 131710478, compound

HRID 1287478Notes

Reaction equation

HRID 1287478 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][C:3]1([CH2:21][OH:22])[CH:18]([CH3:20])[CH3:19].[CH3:23][C:24](=[CH2:26])[CH3:25].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:24]([O:16][C:15](=[O:17])[CH2:14][O:13][C:7]1[CH:6]=[C:5]2[C:10](=[C:9]([Cl:11])[C:8]=1[Cl:12])[C:2](=[O:1])[C:3]([CH:18]([CH3:20])[CH3:19])([CH2:21][O:22][C:3]([CH3:18])([CH3:4])[CH3:2])[CH2:4]2)([CH3:25])([CH3:23])[CH3:26]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 20358452HCID 20358452, compound

Product 1

HCID 131710478HCID 131710478, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (1-oxo-2-hydroxymethyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid (4.0 g., 0.012 mole), isobutylene (6 ml.), chloroform (20 ml.) and concentrated sulfuric acid (0.1 ml.) is sealed from the atmosphere and stirred at 25°C. for two weeks. After this time, the reaction mixture is poured into saturated aqueous sodium bicarbonate. The chloroform layer is separated, washed with water, dried and the chloroform distilled at reduced pressure affording tert.-butyl-(1-oxo-2-isopropyl-2-tert.-butoxymethyl-6,7-dichloro-5-indanyloxy)acetate which is hydrolyzed in a refluxing solution of methanolic potassium hydroxide. Acidification of the hydrolysis solution affords (1-oxo-2-isopropyl-2-tert.-butoxymethyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 148°-149° C. after recrystallization from acetic acid-water.

Workup

  1. customThe chloroform layer is separated
  2. washwashed with water
  3. customdried
  4. distillationthe chloroform distilled at reduced pressure

Sources & evidence

ORD record
ord-91be0ebfb34c4025a8036099b016d278
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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