Dimethylformamide → Hexyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 1003645Notes

Reaction equation

HRID 1003645 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.CN(C=O)C.C(=O)(O)[O-].[Na+].I[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>C1OCCOCCOCCOCCOC1.O>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([O:23][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 125271-IodohexaneHCID 516892Sodium BicarbonateHCID 153890694-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid

Product 1

HCID 18357926Hexyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 962WaterSolvent

Procedure

2 g (5.8 mmol) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid, 30 ml of DMF, 2 drops of 15-crown-5 and 2 g (23.8 mmol) of sodium bicarbonate are introduced into a round-bottomed flask. 3.1 ml (20.8 mmol) of 1-iodohexane are added and the mixture is stirred at room temperature for 24 hours. The reaction medium is poured into water and extracted with ethyl acetate and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. 2 g (80%) of the expected hexyl ester are collected in the form of a pale red oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out after settling
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom2 g (80%) of the expected hexyl ester are collected in the form of a pale red oil

Sources & evidence

ORD record
ord-731e6bf398794ca0a12164303ef6b6e1
Source dataset
uspto-grants-2000_04
Patent number
US06046220

Reaction notes

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