HCID 21474520, compound → HCID 19029760, compound

HRID 2256356Notes

Reaction equation

HRID 2256356 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 recrystallised 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 recrystallised in cyclohexane
  7. custom900 mg (86%) of the expected product of melting point 170°-171° C. are collected

Sources & evidence

ORD record
ord-79a63c73249a476ebf08f54ca7a96a64
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

Loading…