Hydrochloric Acid → HCID 15143606, compound

HRID 1084816Notes

Reaction equation

HRID 1084816 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[OH:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1.Cl>CCCCCC.O1CCCC1>[C:24]([CH2:23][CH2:22][C:21]([O:20][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:27])([OH:26])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 24758Sodium hydrideHCID 160268Dup 654

Product 1

HCID 15143606HCID 15143606, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% in mineral oil; 1.32 g, 0.33 mol) was washed free of mineral oil by stirring in hexane and decanting the solvent. Tetrahydrofuran (75 mL) was added and the suspension was stirred at 0°. A solution of 2-phenylmethyl1-naphthol (7.00 g, 0.030 mol) in tetrahydrofuran (100 mL) was added dropwise. After the mixture was stirred for two hours, a solution of succinic anhydride (3.30 g, 0.033 mol) in tetrahydrofuran (80 mL) was added dropwise. After stirring for one hour at 0°, 1 N hydrochloric acid was added slowly until the mixture was acidic. The tetrahydrofuran was removed on a rotary evaporator and the residue was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water and brine and was dried over MgSO4. Concentration provided a yellow solid, which was recrystallized (1-chlorobutane) to provide the title compound (6.89 g, 69%) as white crystals: mp 139.5°-140.5°; NMR (CDCl3) 7.79 (m, 2H), 7.66 (d, J=7 Hz, IH), 7.47 (m, 2H), 7.3-7.2 (m, 6H), 4.02 (s, 2H), 3.01 (t, J=6 Hz, 2H), 2.81 (t, J=6 Hz, 2H); IR (mull) 3200-2400, 1745, 1714; Calcd. for C21H18O4 : C-75.43 H-5.43; Found C-75.13 H-5.42.

Workup

  1. customdecanting the solvent
  2. additionTetrahydrofuran (75 mL) was added
  3. stirringAfter the mixture was stirred for two hours
  4. stirringAfter stirring for one hour at 0°
  5. customThe tetrahydrofuran was removed on a rotary evaporator
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe organic layer was washed with dilute hydrochloric acid, water and brine
  8. dry with materialwas dried over MgSO4
  9. concentrationConcentration
  10. customprovided a yellow solid, which
  11. customwas recrystallized (1-chlorobutane)

Sources & evidence

ORD record
ord-0624426577a4463794e1811364c15cdc
Source dataset
uspto-grants-1991_04
Patent number
US05006555

Reaction notes

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