Water → 5-(3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)pentyl Acetate

HRID 1278842Notes

Reaction equation

HRID 1278842 reaction equation
[Br:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)(=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C.C(OCC)(=O)C>[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:16][C:3]1[C:2]([Br:1])=[CH:11][C:10]2[C:9]([CH3:12])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]=2[CH:4]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 851405-Bromopentyl acetateHCID 107793113-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 222527755-(3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)pentyl Acetate

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol (10 g, 0.35 mol), 5-bromopentyl acetate (8.15 g) and potassium carbonate (33.6 g) in methyl ethyl ketone (200 ml) is refluxed for 2 hours. The reaction medium is treated with water and ethyl acetate. After separation of the phases by settling, the organic phase is washed twice with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on a column of silica.

Workup

  1. customAfter separation of the phases
  2. washthe organic phase is washed twice with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  5. customThe product is purified by flash chromatography on a column of silica

Sources & evidence

ORD record
ord-0bf45b310f534b5da522b02d9a49f0b8
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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