Sodium Hydroxide → (1-Methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran-1-yl)acetic acid

HRID 1731136Notes

Reaction equation

HRID 1731136 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C:5]1([CH3:18])[C:10]2[CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=2[CH2:8][CH2:7][O:6]1.[OH-].[Na+]>CO.O>[CH3:18][C:5]1([CH2:4][C:3]([OH:19])=[O:2])[C:10]2[CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:9]=2[CH2:8][CH2:7][O:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 536402551-Methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran-1-acetic acid methyl ester

Product 1

HCID 21495330(1-Methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Hydrolysis of this ester to the title compound is effected as follows: The latter ester (11.5 g) is dissolved in 400 ml of methanol and the solution mixed with a solution of 12 g of sodium hydroxide in 100 ml of water. The resulting mixture is kept at room temperature overnight. Methanol is removed by evaporation. The residue is diluted with water. The aqueous solution is extracted repeatedly with ether, and acidified with 6N hydrochloric acid. The resulting precipitate is extracted with ether. The ether extract is dried (MgSO4), filtered and concentrated. The residue is crystallized from benzene to give the title compound, m.p. 179°-180° C, nmr (CDCl3) δ 1.45 (s, 3H), 2.51 (m, 2H), 2.73 (s, 2H), 3.25 (t, 2H), 4.02 (t, 2H), 7.26 (m, 4H), 9.80 (broad, 1H).

Workup

  1. customMethanol is removed by evaporation
  2. additionThe residue is diluted with water
  3. extractionThe aqueous solution is extracted repeatedly with ether
  4. extractionThe resulting precipitate is extracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is crystallized from benzene

Sources & evidence

ORD record
ord-07f367d89deb45b79c601b7af6c9e239
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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