Water → (1-Benzylcyclohex-2-en-1-yl)acetic acid

HRID 890922Notes

Reaction equation

HRID 890922 reaction equation
[O-]Cl=O.[Na+].[OH2:5].[CH2:6]([C:13]1([CH2:19][CH:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CS(C)=O.CCOCC>[CH2:6]([C:13]1([CH2:19][C:20]([OH:5])=[O:21])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22243087(1-Benzylcyclohex-2-en-1-yl)acetaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 22243083(1-Benzylcyclohex-2-en-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of NaH2PO4 (55.3 g), NaClO2 (36.3 g), DMSO (200 mL) and water (375 mL) was added a solution of 3-benzyl-3-formylmethylcyclohexene (57 g) in DMSO (150 mL) during a 3 hour period. After addition, the mixture was stirred overnight and diluted with ether (200 mL). This was extracted with saturated NaHCO3 (3×100 mL). The combined aqueous layer was cooled to 0° C. and acidified to PH=1 with conc. HCl. This was extracted with CH2Cl2 (3×300 mL). The combined organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as thick oil (50 g). MS (MH+=231).

Workup

  1. additionAfter addition
  2. extractionThis was extracted with saturated NaHCO3 (3×100 mL)
  3. extractionThis was extracted with CH2Cl2 (3×300 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-de41880043ba495f9adf2ef3b9cf08ea
Source dataset
uspto-grants-2006_02
Patent number
US07001898B2

Reaction notes

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