Hydrochloric Acid → HCID 18990113, compound

HRID 979255Notes

Reaction equation

HRID 979255 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][C:15]([CH3:25])([CH3:24])[C:14]=4[CH:13]=3)[CH:10]=2)[CH:5]=[C:4]([C:26]([OH:28])=[O:27])[CH:3]=1.[H-].[Na+].[CH3:31]I.Cl>C1COCC1.O.CN(C)C=O>[CH3:31][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:18]([CH3:22])([CH3:23])[CH2:17][CH2:16][C:15]([CH3:24])([CH3:25])[C:14]=4[CH:13]=3)[CH:10]=2)[CH:5]=[C:4]([C:26]([OH:28])=[O:27])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19995384HCID 19995384, compound

Product 1

HCID 18990113HCID 18990113, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.8 g (2.1 mmoles) of the acid obtained in Example 2, dissolved in 10 ml of THF, are added drop by drop to a suspension of sodium hydride (0.113 g; 4.7 mmoles) in 10 ml of THF. After stirring for two hours at room temperature, 10 ml of dimethylformamide and 0.90 g (6.3 mmoles) of methyl iodide are added. After stirring for one hour, the mixture is poured into water and brought to pH 1 (concentrated hydrochloric acid). Following extraction by ether, the organic phase is decanted, then dried and evaporated. The solid thus formed is recrystallized in a mixture of diisopropyl ether (50%) and cyclohexane (50%). In this manner is obtained 0.60 g (74%) of 4-methoxy-6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2 naphthoic acid which melts at 242° C.

Workup

  1. additionare added drop by drop
  2. stirringAfter stirring for one hour
  3. extractionextraction by ether
  4. customthe organic phase is decanted
  5. customdried
  6. customevaporated
  7. customThe solid thus formed
  8. customis recrystallized in a mixture of diisopropyl ether (50%) and cyclohexane (50%)

Sources & evidence

ORD record
ord-174059e0b63e4c4c998a25fead474e73
Source dataset
uspto-grants-1987_05
Patent number
US04666941

Reaction notes

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