Water → HCID 15840104, compound

HRID 1602698Notes

Reaction equation

HRID 1602698 reaction equation
[CH3:1][C:2]1([C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[C:6]2[CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[OH-].[Na+].[OH-].[Li+].O>C1COCC1>[CH3:1][C:2]1([C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[C:6]2[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 15840103HCID 15840103, compound

Product 1

HCID 15840104HCID 15840104, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-methyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2H-1-benzofuran-5-carboxylate (510 mg, 1.35 mmol), sodium hydroxide (0.33 g, 7.9 mmol), lithium hydroxide (0.33 g, 7.9 mmol) and water in THF is stirred at room temperature for 5 days. The mixture is concentrated on a rotary evaporator under vacuum at 40° C. 10 ml of water and 10 ml of ethyl acetate are added. The mixture is acidified with concentrated hydrochloric acid solution to pH 1. After separation of the phases by settling, the organic phase is washed twice with 10 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The solid obtained is washed with heptane.

Workup

  1. concentrationThe mixture is concentrated on a rotary evaporator under vacuum at 40° C
  2. addition10 ml of water and 10 ml of ethyl acetate are added
  3. customAfter separation of the phases
  4. washthe organic phase is washed twice with 10 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  7. customThe solid obtained
  8. washis washed with heptane

Sources & evidence

ORD record
ord-505609fff72d4e0aac8dd3f74ead87a3
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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