Sodium Hydroxide → HCID 11375701, compound

HRID 2110397Notes

Reaction equation

HRID 2110397 reaction equation
[OH-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([C:28]4[CH:29]=[C:30]5[C:35](=[CH:36][CH:37]=4)[CH:34]=[C:33]([C:38]([O:40]C)=[O:39])[CH:32]=[CH:31]5)[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][CH:21]3[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]3)[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>CO>[C:3]12([C:13]3[CH:14]=[C:15]([C:28]4[CH:29]=[C:30]5[C:35](=[CH:36][CH:37]=4)[CH:34]=[C:33]([C:38]([OH:40])=[O:39])[CH:32]=[CH:31]5)[CH:16]=[CH:17][C:18]=3[O:19][CH2:20][CH:21]3[CH2:25][O:24][C:23]([CH3:26])([CH3:27])[O:22]3)[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 10554120HCID 10554120, compound

Product 1

HCID 11375701HCID 11375701, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2 g (50 mmol) of sodium hydroxide and 25 ml of methanol (i.e., 25 ml of a 2N solution of methanolic sodium hydroxide) are added to 1 g (1.9 mmol) of methyl 6-[3-adamantan-1-yl-4-(2,2-dimethyl[1,3]dioxolan-4-ylmethoxy)phenyl]naphthalene-2-carboxylate. The reaction medium is heated at the reflux of methanol for 6 h and then at ambient temperature for 2 days and, finally, evaporated to dryness. The solid residue is taken up in water, and the aqueous phase is acidified to pH=2-3 and extracted with ether. The organic phase is washed with water and then with brine, dried over magnesium sulfate, filtered, and evaporated until only approximately 10 ml of a suspension of the product in ether remains. The crystals are then filtered off and dried. After drying, 862 mg (88%) of a yellowish powder are obtained (mp=287° C.). 1H NMR (CDCl3+drop DMSO-d6) (250 MHz): 1.43 (s, 3H), 1.49 (s, 3H), 1.80 (s, 6H), 2.12 (broad s, 3H), 2.18 (s, 6H), 4.05 (m, 2H), 4.16-4.30 (m, 2H), 4.60 (m, 1H), 7.0 (d, J=8.5 Hz, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.6 (s, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.89-8.00 (m, 3H), 8.09 (d, J=10.0 Hz, 1H), 8.63 (s, 1H).

Workup

  1. temperatureThe reaction medium is heated at the
  2. customfinally, evaporated to dryness
  3. extractionextracted with ether
  4. washThe organic phase is washed with water
  5. dry with materialwith brine, dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated until only approximately 10 ml of a suspension of the product in ether
  8. filtrationThe crystals are then filtered off
  9. customdried
  10. customAfter drying

Sources & evidence

ORD record
ord-52a50cbed63d4b459e6d432da6fa11c9
Source dataset
uspto-grants-2009_04
Patent number
US07517907B2

Reaction notes

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