Ethyl acetate hexane → (3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)-methanol

HRID 2186549Notes

Reaction equation

HRID 2186549 reaction equation
[CH2:1]([C:7]1[C:8]([CH:21]=[O:22])=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(OCC)(=O)C.CCCCCC>C1COCC1>[CH2:1]([C:7]1[C:8]([CH2:21][OH:22])=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 230025113-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-aldehyde

Product 1

HCID 22456873(3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)-methanolYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.14 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-aldehyde (from Example 4.1) in 20 ml of THF was cooled to 0° C. and treated with 13.8 ml of borane-THF complex sol. 1M in THF (3 H eq.). The mixture was stirred at room temperature for 90 min., then cooled back at 0° C. and quenched carefully by the addition of 30 ml of hydrochloric acid 3N. The mixture was stirred at room temperature for 30 min., then was extracted with 3 portions of 100 ml ether. The combined extracts were washed with water (100 ml) and a saturated aqueous sodium chloride solution (100 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo, giving a pale yellow oil. Flash chromatography (SiO2, 10% ethyl acetate/hexane) afforded 3.80 g of the title compound as a colourless oil. 1 H NMR (CDCl3): 7.27 (s, 1H), 7.11 (s, 1H), 4.67 (d, J=5.7 Hz, 2H), 2.59 (t, J=8.3 Hz, 2H), 1.67 (s, 4H), 1.50-1.65 (m, 2H), 1.20-1.45 (m,6H), 1.28 (s, 6H), 1.27 (s, 6H), 0.89 (t, J=6.6 Hz, 3H).

Workup

  1. temperaturecooled back at 0° C.
  2. customquenched carefully by the addition of 30 ml of hydrochloric acid 3N
  3. stirringThe mixture was stirred at room temperature for 30 min.
  4. extractionwas extracted with 3 portions of 100 ml ether
  5. washThe combined extracts were washed with water (100 ml)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customgiving a pale yellow oil

Sources & evidence

ORD record
ord-5edd906f3f4242b5990c9f06618a592d
Source dataset
uspto-grants-2002_06
Patent number
US06403810B2

Reaction notes

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