1-Propanol → 8-Tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine

HRID 260263Notes

Reaction equation

HRID 260263 reaction equation
C(O)CC.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][CH2:19]OC)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].COCOC.COCOCOC>ClCCl>[C:5]([C:9]1[CH:14]=[CH:13][C:12]2[CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:11]=2[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 10311-PropanolHCID 8020Dimethoxymethane2×HCID 12362Bis(methoxymethyl)ether2×HCID 152718851-Tert-butyl-4-(3-methoxymethoxypropyl)benzene

Product 1

HCID 152718948-Tert-butyl-1,3,4,5-tetrahydro-2-benzoxepineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above-mentioned propanol was then converted into 1-tert-butyl-4-(3-methoxymethoxypropyl)benzene by means of dimethoxymethane, in an analogous manner to that described by J. L. Gras et al. in Synthesis 74, (1985), but using 12 equivalents of dimethoxymethane for 1 equivalent of alcohol. The above-mentioned methoxymethylether was then transformed as described by A. Rieche et al., Chem. Ber. 95, 91 (1962) but using dichloromethane as solvent. The concentration of methoxymethylether in this solvent varied between 0.1 and 0.3 M. The reaction product was purified by chromatography to provide 8-tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine (yield 67%, purety>99%).

Workup

  1. customGras et al. in Synthesis 74, (1985),
  2. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-ce2003d8cdd945edaebca872af7889cb
Source dataset
uspto-grants-1996_06
Patent number
US05527769

Reaction notes

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