Hydrochloric Acid → HCID 54162800, compound

HRID 249466Notes

Reaction equation

HRID 249466 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]2[CH2:17][CH2:16]2)[C:10]=1[CH3:18].Cl.C[O-].[Na+]>CO>[CH:15]1([C:11]2[C:10]([CH3:18])=[C:9]([CH:14]=[CH:13][CH:12]=2)[CH2:8][OH:7])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 19761787HCID 19761787, compound

Product 1

HCID 54162800HCID 54162800, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Elimination of the protective group: 16.7 g of 3-cyclopropyl-2-methylbenzyl tetrahydro-2-pyranyl ether in 180 ml of methanol are stirred overnight at room temperature with 10.8 ml of concentrated hydrochloric acid. The mixture is neutralized with sodium methylate solution while cooling with ice and is then evaporated down. Water is added to the residue, which is then extracted several times with ether. The combined ether extracts are washed with water, dried and evaporated down. The crude product (11.5 g) is purified by column chromatography over silica gel using toluene as the mobile phase. 8.9 g of 3-cyclopropyl-2-methylbenzyl alcohol (Example 100) are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customis then evaporated down
  3. additionWater is added to the residue, which
  4. extractionis then extracted several times with ether
  5. washThe combined ether extracts are washed with water
  6. customdried
  7. customevaporated down
  8. customThe crude product (11.5 g) is purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-253e938fb97842a9b3d1f5ba9c8b7472
Source dataset
uspto-grants-1993_05
Patent number
US05214187

Reaction notes

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