Benzyl Bromide → Benzyl 2-hydroxystearate

HRID 489074

Reaction equation

HRID 489074 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([OH:5])=[O:4].CC(C)([O-])C.[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]([O:5][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 694172-Hydroxystearic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 22035791Benzyl 2-hydroxystearate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of DL-2-hydroxystearic acid (3.0 g, 10 mmole) in 20 ml dry DMF was added potassium tert-butoxide (1.23 g, 11 mmole) and the mixture was stirred for one hour at 60° C. Benzyl bromide (2.14 g, 12.5 mmole) was added and the mixture was stirred for six hours at 80° C. The mixture was evaporated under reduced pressure and 100 ml ethyl acatate was added. The organic phase was separated and washed four times with water. The organic phase was dried with sodium sulfate and concentrated in vacuo. The product was isolated by silica gel column chromatography. Yield: 3.3 g

Workup

  1. stirringthe mixture was stirred for six hours at 80° C
  2. customThe mixture was evaporated under reduced pressure and 100 ml ethyl acatate
  3. additionwas added
  4. customThe organic phase was separated
  5. washwashed four times with water
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-a8bb89d7b8f94103849074a5d5070bc5
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Linked notes

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