Hydrochloric Acid → HCID 9923202, compound

HRID 1976757Notes

Reaction equation

HRID 1976757 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:22]([CH3:24])([CH3:23])[CH2:21][CH2:20][C:19](=[O:25])[C:18]=1[CH3:26])(=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:22]([CH3:23])([CH3:24])[CH2:21][CH2:20][C:19](=[O:25])[C:18]=1[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21999132HCID 21999132, compound

Product 1

HCID 9923202HCID 9923202, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(12-acetoxydodecyl)-2,4,4-trimethyl-2-cyclohexene-1-one (132 mg, 0.36 mmol, 1 eq.) in dry methanol (8 ml) was added water (3 drops) and K2CO3 (74 mg, 0.54 mmol, 1.5 eq.). After stirring at room temperature for 2.5 hours the solution was neutralized at pH 7 with HCl 5%, extracted with ether, dried with MgSO4 and concentrated in vacuo. The residue was purified by chromatography over silica gel, eluting with hexane-AcOEt (8-2 to 7-3) to give 3-(12-hydroxydodecy)-2,4,4-trimethyl-2-cyclohexen-1-one as a colorless oil (94 mg, 81%).

Workup

  1. extractionextracted with ether
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography over silica gel
  5. washeluting with hexane-AcOEt (8-2 to 7-3)

Sources & evidence

ORD record
ord-aa2a142e86f34ea282726ef68e7bcc58
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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