HCID 21474520, compound → HCID 19029760, compound

HRID 2260168Notes

Reaction equation

HRID 2260168 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([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)=[O:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:29][Li]>C1COCC1>[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([OH:14])([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)[CH3:29])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 21474520HCID 21474520, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19029760HCID 19029760, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 g (2.6 mmol) of 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoylmethoxy)benzoic acid and 50 ml of THF are introduced into a three-necked flask under a stream of nitrogen. 5.3 ml (8.3 mmol) of a solution of methyl lithium in THF (1.6M) are added dropwise at -78° C. and the reaction mixture is stirred for 12 hours at room temperature. It is poured into ice-water, acidified to pH=1 and extracted with ethyl ether, and the organic phase is separated, dried over magnesium sulphate and evaporated. The residue obtained is recrystalised in cyclohexane and 900 mg (86%) of the expected product of melting point 170°-171° C. are collected.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis recrystalised in cyclohexane
  7. custom900 mg (86%) of the expected product of melting point 170°-171° C. are collected

Sources & evidence

ORD record
ord-2490a0f7ff3049c592ee50ed48ad4eeb
Source dataset
uspto-grants-1995_12
Patent number
US05476860

Reaction notes

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