Dichloromethane → HCID 19767559, compound

HRID 1590559Notes

Reaction equation

HRID 1590559 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]=2[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19]C(Cl)Cl.ClCCl>>[C:1]([C:5]1[CH:14]=[C:13]([CH:18]=[O:19])[C:12]2[CH2:11][CH2:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]=2[C:6]=1[OH:17])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 21004Methane, dichloromethoxy-HCID 19767568HCID 19767568, compound

Product 1

HCID 19767559HCID 19767559, compoundYield 90%

Procedure

To a solution of 2-tert-butyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthol (9.5 g, 40.5 mmole) and 1,1-dichloromethyl methyl ether (5.17 g, 45 mmole) in dry dichloromethane (200 ml) stannic chloride (15.63 g, 60 mmole) was added dropwise at -58°. The mixture was warmed to 0° over 45 minutes, poured into ice water (300 ml) and extracted with diethyl ether (3×150 ml). The ether extracts were washed with water and aqueous saturated sodium chloride, dried and evaporated to give 3-tert-butyl-5,5-dimethyl-4-hydroxy-5,6,7,8-tetrahydro-1-naphthaldehyde as a crystalline solid (9.49 g, 90%), m.p. 143°-45°.

Workup

  1. temperatureThe mixture was warmed to 0° over 45 minutes
  2. extractionextracted with diethyl ether (3×150 ml)
  3. washThe ether extracts were washed with water and aqueous saturated sodium chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-dd9b5790150a4df6929878388ecb1a3b
Source dataset
uspto-grants-1993_04
Patent number
US05204336

Reaction notes

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