Benzyl Alcohol → HCID 18370146, compound

HRID 484752Notes

Reaction equation

HRID 484752 reaction equation
[CH3:1][CH:2]([CH3:10])[CH2:3][CH2:4][C:5](=[O:9])[C:6]([OH:8])=[O:7].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:26](O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][CH:2]([CH3:10])[CH2:3][CH2:4][C:5](=[O:9])[C:6]([O:8][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:7]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 1293965126395-06-2

Product 1

HCID 18370146HCID 18370146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 5-methyl-2-oxohexanoic acid (0.288 g.) in methylene chloride (1 ml.) was added during 15 minutes to a stirred solution of dicyclohexylcarbodiimide (0.412 g.) and benzyl alcohol (0.432 g.) in methylene chloride (10 ml.) which was cooled to -15° C., and the mixture was stirred at that temperature for 1 hour, then at laboratory temperature for 30 minutes, and was then evaporated to dryness. Water (1 ml.), diethyl ether (2 ml.) and acetic acid (0.01 ml.) were added and the mixture was kept at laboratory temperature for 12 hours and then evaporated to dryness. The residue was purified by chromatography on a silica gel column using toluene as eluant and there was thus obtained benzyl 5-methyl-2-oxohexanoate as an oil.

Workup

  1. waitat laboratory temperature for 30 minutes
  2. customwas then evaporated to dryness
  3. additionWater (1 ml.), diethyl ether (2 ml.) and acetic acid (0.01 ml.) were added
  4. waitthe mixture was kept at laboratory temperature for 12 hours
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-80e098dd023b4de6a0e2fa2858024579
Source dataset
uspto-grants-1985_08
Patent number
US04533656

Reaction notes

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