Sodium Hydroxide → HCID 66652162, compound

HRID 418960Notes

Reaction equation

HRID 418960 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH2:7][CH:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH:9]3[CH2:18][CH2:17][CH2:16][CH:10]3[C:11]=2[CH:12]=[C:13]([OH:15])[CH:14]=1)=[O:4].[OH-].[Na+]>C(O)C>[OH:15][C:13]1[CH:14]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH2:7][CH:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH:9]3[CH2:18][CH2:17][CH2:16][CH:10]3[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66652171HCID 66652171, compound

Product 1

HCID 66652162HCID 66652162, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 8-Hydroxy-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalene-6-carboxylic acid methyl ester (0.013 g, 0.038 mmol), ethanol (3 ml), and NaOH (1.5 ml, 2N) and heat at 45° C. for 1.5 hours. Acidify with 1 N HCl and extract with ethyl acetate. Wash 1× with water, dry over anhydrous sodium sulfate and concentrate in vacuo to yield the titled compound (0.010 g, 84%) as a white residue. 1H NMR (CD3OD) 7.1 (d, J=7.5 Hz, 2H), 7.08 (s, 1H), 6.8 (s, 1H), 6.7 (d, J=7.5 Hz, 2H), 3.4 (m, 1H), 3.15 (m, 1H), 3.0 (m, 2H), 2.55(m, 1H) 2.2 (m, 1H), 1.6-1.2. MS m/z 323 (M−1).

Workup

  1. extractionAcidify with 1 N HCl and extract with ethyl acetate
  2. washWash 1× with water
  3. dry with materialdry over anhydrous sodium sulfate
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-275a37f52d1d43079dfd73c1f11b0ff7
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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