Water → HCID 19767568, compound

HRID 1590558Notes

Reaction equation

HRID 1590558 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:10]([OH:12])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[C:14](O)([CH3:17])([CH3:16])[CH3:15].O>C(O)(=O)C>[C:14]([C:9]1[CH:8]=[CH:7][C:6]2[CH2:5][CH2:4][CH2:3][C:2]([CH3:13])([CH3:1])[C:11]=2[C:10]=1[OH:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 6386tert-ButanolHCID 19767569HCID 19767569, compound

Product 1

HCID 19767568HCID 19767568, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 8,8-dimethyl-5,6,7,8-tetrahydro-1-naphthol (10.1 g, 57.3 mmole) and tert-butanol (4.25 g, 57.3 mmole) in glacial acetic acid (30 ml) 90% aqueous sulphuric acid (3.0 ml) was added. The mixture was stirred at 40° for 3 hours, poured into water (100 ml) and extracted with diethylether (2×200 ml). The ethereal extract was washed with water and with aqueous saturated sodium chloride, dried and evaporated. The residue was chromatographed on silica gel using a n-pentane: dichloromethane (1:1) mixture to give 2-tert-butyl-8,8-dimethyl-5,6,7,8-tetrahydro-1-naphthol as a colourless oil (9.5 g, 71%).

Workup

  1. extractionextracted with diethylether (2×200 ml)
  2. extractionThe ethereal extract
  3. washwas washed with water and with aqueous saturated sodium chloride
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using a n-pentane: dichloromethane (1:1) mixture

Sources & evidence

ORD record
ord-7de82c18d6ed48e6ba0a9f875e609bd2
Source dataset
uspto-grants-1993_04
Patent number
US05204336

Reaction notes

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