Lithium Hydroxide → HCID 17867247, compound

HRID 1602709Notes

Reaction equation

HRID 1602709 reaction equation
[CH3:1][C:2]1[C:3]([C:16]2([CH3:29])[C:20]3[CH:21]=[CH:22][C:23]([C:25]([O:27]C)=[O:26])=[CH:24][C:19]=3[O:18][CH2:17]2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-].[Na+].[OH-].[Li+].CCOC(C)=O>CCCCCCC>[CH3:1][C:2]1[C:3]([C:16]2([CH3:29])[C:20]3[CH:21]=[CH:22][C:23]([C:25]([OH:27])=[O:26])=[CH:24][C:19]=3[O:18][CH2:17]2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19612294HCID 19612294, compound

Product 1

HCID 17867247HCID 17867247, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A mixture of methyl 3-(3-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-3-methyl-2H-1-benzofuran-6-carboxylate (140 mg, 0.36 mmol), sodium hydroxide (0.06 g, 1.54 mmol) and lithium hydroxide (0.06 g, 1.54 mmol) is stirred at room temperature for 24 h. The mixture is concentrated on a rotary evaporator under vacuum at 40° C. 10 ml of water and 10 ml of ethyl ether 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 product is obtained by recrystallization from a heptane/ethyl ether mixture (3/1). (90 EtOAc, 10 heptane) (Rf: 0.56).

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 ether 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 product is obtained by recrystallization from a heptane/ethyl ether mixture (3/1)

Sources & evidence

ORD record
ord-af673c62c7be45a1b2365afe8dea2297
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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