Water → 4-Phenethyloxycarbonyloxy-decanoic Acid 3,7-dimethyl-oct-6-enyl-ester

HRID 2304959Notes

Reaction equation

HRID 2304959 reaction equation
[CH3:1][CH:2]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH2:3][CH2:4][O:5][C:6](=[O:17])[CH2:7][CH2:8][CH:9]([OH:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].N1C=CC=CC=1.[CH2:30]([O:38][C:39](Cl)=[O:40])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>O1CCCC1>[CH3:1][CH:2]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH2:3][CH2:4][O:5][C:6](=[O:17])[CH2:7][CH2:8][CH:9]([O:16][C:39]([O:38][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:40])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 159175902-Phenylethyl chloroformateHCID 542824114-Hydroxy-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

Product 1

HCID 545720404-Phenethyloxycarbonyloxy-decanoic Acid 3,7-dimethyl-oct-6-enyl-esterYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 3 g 4-hydroxy-decanoic acid 3,7-dimethyl-oct-6-enyl ester and 1.45 g pyridine in 7 ml tetrahydrofuran was slowly added a solution of 1.87 g chlorocarbonic acid phenethyl ester (Schiving et al., Bull. Soc. Chim. Fr. (4), 43, 1928, 858) in 7 ml tetrahydrofuran. The mixture was stirred for 16 hours. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel to give 3.91 g of a colorless liquid.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-55216e16f4cb4bd5a5674441b5606513
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

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