Hydrochloric Acid → HCID 20358449, compound

HRID 1679743Notes

Reaction equation

HRID 1679743 reaction equation
CC1C(C2C=CC=CC=2)C2C(=C(Cl)C(Cl)=C(OC)C=2)C1=O.CI.CC(C)([O-])C.[K+].Cl.[O:31]=[C:32]1[C:40]2[C:35](=[CH:36][C:37]([O:43][CH2:44]C(O)=O)=[C:38]([Cl:42])[C:39]=2[Cl:41])[C:34]([CH3:54])([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:33]1([CH3:56])[CH3:55]>CN(C)C=O>[CH3:55][C:33]1([CH3:56])[C:34]([CH3:54])([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:35]2[C:40](=[C:39]([Cl:41])[C:38]([Cl:42])=[C:37]([O:43][CH3:44])[CH:36]=2)[C:32]1=[O:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 12395570HCID 12395570, compoundHCID 20358465HCID 20358465, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 20358449HCID 20358449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-3-phenyl-5-methoxy-6,7-dichloro-1-indanone (9.63 g., 0.03 mole) and methyl iodide (18.7 ml., 0.3 mole) dissolved in dimethylformamide (100 ml.) under nitrogen at 25° C. are treated with potassium tert-butoxide (6.72 g., 0.06 mole) portionwise with intermittent cooling in an ice-water bath over a 5 hour period. After exhaustive alkylation, i.e., after the addition of methyl iodide (3 × 20 ml.) followed by potassium tert-butoxide (5 g.), this procedure repeated until the addition of the base gives no green color, acidified with 6N hydrochloric acid to precipitate the product which on trituration with hexane and crystallization from acetic acid: water, 1:1, gives 3.49 g. of (1-oxo-2,2,3-trimethyl-3-phenyl-6,7-dichloro-5-indanyloxy)acetic acid which melts at 189°-190° C.

Workup

  1. temperaturewith intermittent cooling in an ice-water bath over a 5 hour period
  2. additionthis procedure repeated until the addition of the base
  3. customgives no green color
  4. customto precipitate the product which on trituration
  5. customwith hexane and crystallization from acetic acid
  6. customwater, 1:1, gives 3.49 g

Sources & evidence

ORD record
ord-2d0992bf8db14b0eb13ed1619e3f44fa
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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